IL121066A - Process for the preparation of 5-bromo-2-fluorobenzeneboronic acid - Google Patents

Process for the preparation of 5-bromo-2-fluorobenzeneboronic acid

Info

Publication number: IL121066A
Authority: IL; Israel
Prior art keywords: bromo; lithium; fluorophenyl; acid; fluorobenzeneboronate
Prior art date: 1996-06-14

Application number

IL12106697A

Other languages

English (en)

Other versions

IL121066A0 (en

Original Assignee

American Cyanamid Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-06-14

Filing date

1997-06-12

Publication date

2004-03-28

1997-06-12 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1997-06-12 Priority to IL12910997A priority Critical patent/IL129109A/en

1997-11-20 Publication of IL121066A0 publication Critical patent/IL121066A0/xx

1999-03-22 Priority to IL12910999A priority patent/IL129109A0/xx

2004-03-28 Publication of IL121066A publication Critical patent/IL121066A/en

Links

238000000034 method Methods 0.000 title claims abstract description 52
IGBDPRKNAFOOGY-UHFFFAOYSA-N (5-bromo-2-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC(Br)=CC=C1F IGBDPRKNAFOOGY-UHFFFAOYSA-N 0.000 title claims abstract description 45
238000002360 preparation method Methods 0.000 title claims abstract description 15
229910052744 lithium Inorganic materials 0.000 claims description 38
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
CGMYPZZMSOSDEW-UHFFFAOYSA-N [Li]C1=CC(Br)=CC=C1F Chemical compound [Li]C1=CC(Br)=CC=C1F CGMYPZZMSOSDEW-UHFFFAOYSA-N 0.000 claims description 19
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
-1 lithium cyclic amide Chemical class 0.000 claims description 11
230000003301 hydrolyzing effect Effects 0.000 claims description 10
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 10
AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 7
229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
239000011707 mineral Substances 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical group COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 6
150000007524 organic acids Chemical class 0.000 claims description 4
125000001033 ether group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 13
239000000575 pesticide Substances 0.000 abstract description 4
150000002148 esters Chemical class 0.000 abstract description 2
239000002728 pyrethroid Substances 0.000 abstract description 2
MKHDDTWHDFVYDQ-UHFFFAOYSA-N 2,4-dibromo-1-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1Br MKHDDTWHDFVYDQ-UHFFFAOYSA-N 0.000 description 7
YPTHSYKJDRMAJY-UHFFFAOYSA-N 5-bromo-2-fluorophenol Chemical compound OC1=CC(Br)=CC=C1F YPTHSYKJDRMAJY-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
238000010586 diagram Methods 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 6
150000002367 halogens Chemical class 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
239000000203 mixture Substances 0.000 description 6
235000010755 mineral Nutrition 0.000 description 5
239000000243 solution Substances 0.000 description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
ZGPYVJBTCRCSKR-UHFFFAOYSA-N 4-bromo-2-(5-bromo-2-fluorophenoxy)-1-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1OC1=CC(Br)=CC=C1F ZGPYVJBTCRCSKR-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 3
229910001623 magnesium bromide Inorganic materials 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
229910052723 transition metal Inorganic materials 0.000 description 3
150000003624 transition metals Chemical class 0.000 description 3
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
RNTGKISRXVFIIP-UHFFFAOYSA-N 1,2-dibromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C(Br)=C1 RNTGKISRXVFIIP-UHFFFAOYSA-N 0.000 description 2
GREWZYRZMVYLBQ-UHFFFAOYSA-N 4-bromo-1-fluoro-2-phenoxybenzene Chemical compound FC1=CC=C(Br)C=C1OC1=CC=CC=C1 GREWZYRZMVYLBQ-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000005103 alkyl silyl group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000011260 aqueous acid Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
JCIVHYBIFRUGKO-UHFFFAOYSA-N lithium;2,2,6,6-tetramethylpiperidine Chemical compound [Li].CC1(C)CCCC(C)(C)N1 JCIVHYBIFRUGKO-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 1
IPWBFGUBXWMIPR-UHFFFAOYSA-N 1-bromo-2-fluorobenzene Chemical compound FC1=CC=CC=C1Br IPWBFGUBXWMIPR-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
XGBBCUALFPDZIK-UHFFFAOYSA-N OBO.FC1=CC=C(Br)C=C1 Chemical compound OBO.FC1=CC=C(Br)C=C1 XGBBCUALFPDZIK-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
239000012267 brine Substances 0.000 description 1
238000010961 commercial manufacture process Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000284 extract Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
ZLRWTBOIOQQDBJ-UHFFFAOYSA-N lithium;benzylazanide Chemical compound [Li+].[NH-]CC1=CC=CC=C1 ZLRWTBOIOQQDBJ-UHFFFAOYSA-N 0.000 description 1
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
UPRXAOPZPSAYHF-UHFFFAOYSA-N lithium;cyclohexyl(propan-2-yl)azanide Chemical compound CC(C)N([Li])C1CCCCC1 UPRXAOPZPSAYHF-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

IL12106697A 1996-06-14 1997-06-12 Process for the preparation of 5-bromo-2-fluorobenzeneboronic acid IL121066A (en)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
IL12910997A IL129109A (en)	1996-06-14	1997-06-12	Process for the preparation of fluoroolefin compounds
IL12910999A IL129109A0 (en)	1996-06-14	1999-03-22	A process for the preparation of fluoroolefin compounds

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US66375596A	1996-06-14	1996-06-14

Publications (2)

Publication Number	Publication Date
IL121066A0 IL121066A0 (en)	1997-11-20
IL121066A true IL121066A (en)	2004-03-28

Family

ID=24663147

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12106697A IL121066A (en)	1996-06-14	1997-06-12	Process for the preparation of 5-bromo-2-fluorobenzeneboronic acid

Country Status (13)

Country	Link
EP (1)	EP0812847B1 (de)
JP (1)	JPH1059980A (de)
KR (1)	KR100514980B1 (de)
CN (2)	CN1244531C (de)
AT (1)	ATE224901T1 (de)
BR (1)	BR9703531A (de)
DE (1)	DE69715733T2 (de)
DK (1)	DK0812847T3 (de)
ES (1)	ES2184033T3 (de)
IL (1)	IL121066A (de)
PL (1)	PL185310B1 (de)
TW (1)	TW369520B (de)
ZA (1)	ZA975173B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2415193A (en) *	2004-06-19	2005-12-21	F2 Chemicals Ltd	Fluorinated arylboronic acids
JP5187025B2 (ja) *	2008-06-26	2013-04-24	Ｄｉｃ株式会社	フルオロナフトール誘導体の製造方法
US8871970B2 (en)	2008-12-25	2014-10-28	Nippon Soda Co., Ltd.	Process for producing organolithium compound and process for producing substituted aromatic compound
WO2012114347A1 (en) *	2011-02-21	2012-08-30	Avra Laboratories Pvt. Ltd.	Synthesis of chiral substituted benzenes and related aromatic compounds containing 1,2 diols protected as diacetal groups
JP2012232924A (ja) *	2011-04-28	2012-11-29	Tosoh Corp	新規なナフチルボロン酸化合物及びその製造法
CN103570753A (zh) *	2013-11-13	2014-02-12	大连九信生物化工科技有限公司	一种芳基硼酸化合物的制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2579310B2 (ja) *	1986-03-13	1997-02-05	ブリティッシュ・テクノロジー・グループ・リミテッド	殺虫剤製造用中間体
GB2226315B (en) *	1986-03-13	1991-02-06	Nat Res Dev	Intermediates useful in the production of pesticides
DE59108963D1 (de) *	1990-02-01	1998-05-20	Merck Patent Gmbh	Verfahren zur Umsetzung von fluorierten Aromaten mit Elektrophilen

1997
- 1997-05-27 TW TW086107146A patent/TW369520B/zh active
- 1997-06-11 ZA ZA975173A patent/ZA975173B/xx unknown
- 1997-06-11 BR BR9703531A patent/BR9703531A/pt not_active Application Discontinuation
- 1997-06-11 KR KR1019970023991A patent/KR100514980B1/ko not_active Expired - Fee Related
- 1997-06-12 ES ES97304114T patent/ES2184033T3/es not_active Expired - Lifetime
- 1997-06-12 JP JP9169671A patent/JPH1059980A/ja not_active Ceased
- 1997-06-12 DK DK97304114T patent/DK0812847T3/da active
- 1997-06-12 DE DE69715733T patent/DE69715733T2/de not_active Expired - Fee Related
- 1997-06-12 AT AT97304114T patent/ATE224901T1/de not_active IP Right Cessation
- 1997-06-12 IL IL12106697A patent/IL121066A/en not_active IP Right Cessation
- 1997-06-12 EP EP97304114A patent/EP0812847B1/de not_active Expired - Lifetime
- 1997-06-13 CN CNB011377569A patent/CN1244531C/zh not_active Expired - Fee Related
- 1997-06-13 PL PL97320554A patent/PL185310B1/pl not_active IP Right Cessation
- 1997-06-13 CN CN97112744A patent/CN1087743C/zh not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ATE224901T1 (de)	2002-10-15
KR980002054A (ko)	1998-03-30
CN1244531C (zh)	2006-03-08
KR100514980B1 (ko)	2006-01-27
EP0812847B1 (de)	2002-09-25
DK0812847T3 (da)	2002-10-14
CN1403430A (zh)	2003-03-19
DE69715733D1 (de)	2002-10-31
ZA975173B (en)	1998-12-11
CN1168887A (zh)	1997-12-31
DE69715733T2 (de)	2003-05-22
IL121066A0 (en)	1997-11-20
CN1087743C (zh)	2002-07-17
JPH1059980A (ja)	1998-03-03
ES2184033T3 (es)	2003-04-01
EP0812847A1 (de)	1997-12-17
PL320554A1 (en)	1997-12-22
PL185310B1 (pl)	2003-04-30
TW369520B (en)	1999-09-11
BR9703531A (pt)	1998-10-06

Legal Events

Date	Code	Title	Description
2004-09-27	KB	Patent renewed
2008-02-10	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
Chen et al.	1980	The synthesis and reactins of ortho bromophenyllithium
Friedman et al.	1974	Halopolycarbon homologation
Smith et al.	1984	Regioselective synthesis of allyltrimethylsilanes from allylic halides and allylic sulfonates. Application to the synthesis of 2, 3-bis (trimethylsilyl) alk-1-enes
Dabdoub et al.	1988	Acetylenic tellurides: synthesis and reactivity
Allison et al.	1983	An unprecedented bis (carbyne) cluster rearrangement involving simultaneous coupling and decoupling of carbyne fragments: a new homogeneous model for carbon-carbon bond forming and bond breaking on surfaces
JP2579310B2 (ja)	1997-02-05	殺虫剤製造用中間体
EP0812847B1 (de)	2002-09-25	Verfahren zur Herstellung von 5-Brom-2-Fluorbenzolboronsäure
US7632969B2 (en)	2009-12-15	Process for the preparation of perfluoroalkylphosphines and the use thereof as perfluoroalkylating reagents
Oostveen et al.	1980	A novel route to 1-alkynyl ethers via organocopper (I)-induced 1, 3-substitution in 1-iodo-1-methoxypropadiene
US5962742A (en)	1999-10-05	Process for the preparation of 5-bromo-2 fluorobenzeneboronic acid
JPH02311485A (ja)	1990-12-27	含フッ素有機ケイ素化合物及びその製造方法
US6198008B1 (en)	2001-03-06	Process for the preparation of 5-bromo-2-fluorobenzeneboronic acid
Barluenga et al.	1994	Preparation and reactivity of new. beta.-nitrogen-functionalized vinylic organolithium compounds from secondary aliphatic allylamines
Cabezas et al.	1999	Stereospecific synthesis of (E, Z)-and (Z, Z)-hexadeca-10, 12-dienal. Sex pheromone components of Diaphania hyalinata
HK1006091A (en)	1999-02-12	Process for the preparation of 5-bromo-2-fluorobenzeneboronic acid
IL129109A (en)	2004-09-27	Process for the preparation of fluoroolefin compounds
Mandai et al.	1984	Synthesis and highly regioselective Diels-Alder reaction of functionalized isoprenes involving a terminal alkoxy group and chemical modification of the resulting adducts
CN1167748A (zh)	1997-12-17	制备杀虫剂氟烯烃化合物的方法和中间体化合物
JPH1059980A5 (ja)	2005-04-14	５−ブロモ−２−フルオロベンゼンボロン酸の製造方法
Tarasova et al.	1996	Metallation and functionalization of 1‐allenylpyrrole
JP2017002002A (ja)	2017-01-05	含フッ素有機化合物及びこれとグリニャール試薬によるビアリール化合物の製造方法
GB2226315A (en)	1990-06-27	Organometallic 2-fluoro-5-bromophenyl compound
US5684111A (en)	1997-11-04	Silylated dioxolane polymers and monomeric compounds
Andringa et al.	1990	The Copper Halide-Catalyzed Mono-Substitution of Bromine in α,-dibromoalkanes by Grignard reagents. A Reinvestigation
CN112745343B (zh)	2024-03-19	一种三乙氧基氯硅烷的工业化合成方法