CH211773A - Process for the preparation of 2,5-dichloro-4-nitrophenyl-1-trifluoromethylsulfone. - Google Patents

Process for the preparation of 2,5-dichloro-4-nitrophenyl-1-trifluoromethylsulfone.

Info

Publication number
CH211773A
CH211773A CH211773DA CH211773A CH 211773 A CH211773 A CH 211773A CH 211773D A CH211773D A CH 211773DA CH 211773 A CH211773 A CH 211773A
Authority
CH
Switzerland
Prior art keywords
nitrophenyl
dichloro
trifluoromethylsulfone
preparation
parts
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
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.)
Filing date
Publication date
Application filed by Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH211773A publication Critical patent/CH211773A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung von     2.5-Dichlor-4-nitrophenyl-l-trifluormethylsulfon.       Gegenstand des vorliegenden Zusatz  patentes ist ein Verfahren zur     Hersfellung     von 2 . 5 -     Dichlor    - 4 -     nitrophenyl    -1-     trif        luor-          methylsulfon,    welches dadurch gekennzeich  net ist, dass man auf     2.5-Dichlorphenyl-l-          trifluormethylsulfid    Salpetersäure in Gegen  wart von Schwefelsäure einwirken lässt und  das so erhaltene ? .     5-Dichlor-4-nitrophenyl-          1-trifluormethylsulfoxyd    oxydiert.  



  Die erhaltene Verbindung stellt einen  wertvollen Ausgangsstoff für die Herstel  lung von Farbstoffen und Arzneimitteln dar.         Beispiel:       In 250     Volumteile    eines Gemisches aus       90/-0    reiner Salpetersäure und     10%    Mono  hydrat lässt man 124 Gewichtsteile 2.     5-Di-          chlorphenyl-l-trifluormethylsulfid    bei 50 bis  60   C einfliessen. Man rührt noch kurze Zeit  bei 7 0 bis<B>80'</B> C nach und gibt dann auf  Eis. Das ausgeschiedene     2.5-Dichlor-4-ni-          trophenyl-l-trifluormethylsulfoxyd    wird ab-    gesaugt und ausgewaschen. Man erhält es  in sehr guter Ausbeute als gelblich gefärb  tes Pulver.

   Durch     Umkristallisieren,    bei  spielsweise aus Methylalkohol, erhält man  dicke Kristalle, die bei 99 bis<B>100'</B> C  schmelzen.  



  62 Gewichtsteile 2     .5-Dichlor-4-nitrophe-          nyl-l-trifluormethylsulfoxyd    werden in etwa  150     Volumteilen    Eisessig gelöst. In die Lö  sung trägt man bei     etwa    40   C unter Rüh  ren 20 bis 25 Gewichtsteile     Chromtrioxyd     ein. Nach dem Eintragen erhitzt man die  Flüssigkeit noch eine     Stunde    auf 70 bis  <B>80'</B> C. Man verdünnt dann mit Wasser und  saugt das abgeschiedene 2.     5-Dichlor-4-nitro-          phenyl-l-trifluormethylsulfon    ab.

      Die so erhaltene, bisher nicht bekannte ,  Verbindung bildet nach dem     UmkristaTlisie-          ren,    beispielsweise aus Benzin, schwach gelb  lich gefärbte Kristalle, die     bei   <B>60'</B> C  schmelzen.



  Process for the preparation of 2,5-dichloro-4-nitrophenyl-1-trifluoromethylsulfone. The subject of the present additional patent is a process for the production of 2. 5 - dichloro - 4 - nitrophenyl -1- trifluoromethylsulfone, which is characterized by the fact that 2.5-dichlorophenyl-l-trifluoromethyl sulfide is allowed to act in the presence of sulfuric acid and the? . 5-dichloro-4-nitrophenyl-1-trifluoromethylsulfoxide is oxidized.



  The compound obtained is a valuable starting material for the production of dyes and pharmaceuticals. Example: 124 parts by weight of 2.5-dichlorophenyl-1 are added to 250 parts by volume of a mixture of 90 / -0 pure nitric acid and 10% monohydrate. Flow in trifluoromethyl sulfide at 50 to 60 C. The mixture is stirred for a short time at 70 to 80 ° C. and then poured onto ice. The precipitated 2,5-dichloro-4-nitrophenyl-1-trifluoromethylsulfoxide is filtered off with suction and washed out. It is obtained in a very good yield as a yellowish powder.

   Recrystallization, for example from methyl alcohol, gives thick crystals which melt at 99 to 100 ° C.



  62 parts by weight of 2 .5-dichloro-4-nitrophenyl-1-trifluoromethyl sulfoxide are dissolved in about 150 parts by volume of glacial acetic acid. In the solution one carries 20 to 25 parts by weight of chromium trioxide at about 40 C with stirring. After the introduction, the liquid is heated to 70 to 80 ° C. for a further hour. It is then diluted with water and the 2. 5-dichloro-4-nitro-phenyl-1-trifluoromethylsulfone which has separated out is filtered off with suction.

      The compound obtained in this way, previously unknown, forms, after recrystallization, for example from gasoline, pale yellowish-colored crystals which melt at <B> 60 '</B> C.

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Herstellung von 2.5-I)i- chlor - 4 -nitrophenyl -1- trif luor methy 1s nlfon, dadurch gekennzeichnet, dass man auf ? . 5- Dichlorphenyl-1-trifluormethylsulfid Sal petersäure in Gegenwart von Schwefelsäure einwirken lässt und das so erhaltene ? . <B> PATENT CLAIM: </B> Process for the production of 2.5-I) i-chloro - 4 -nitrophenyl -1- trifluoromethy 1s nlfon, characterized in that one on? . 5- dichlorophenyl-1-trifluoromethyl sulfide lets nitric acid act in the presence of sulfuric acid and the? . 3-Di- chlor-4-nitrophenyl-l -trifluormethv lsulfozvd oxydiert. Die so erhaltene neue Verbindung bildet nach dem L rnlzristallisieren, beispielsweise aus Benzin, sehwach gelblich gefärbte Kri stalle. die bei<B>60'</B> C schmelzen. 3-dichloro-4-nitrophenyl-1-trifluoromethane is sulfo-oxidized. The new compound obtained in this way forms, after crystallization, for example from gasoline, slightly yellowish colored crystals. which melt at <B> 60 '</B> C.
CH211773D 1937-10-05 1938-09-29 Process for the preparation of 2,5-dichloro-4-nitrophenyl-1-trifluoromethylsulfone. CH211773A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE210338X 1937-10-05
DE211773X 1937-10-05

Publications (1)

Publication Number Publication Date
CH211773A true CH211773A (en) 1940-10-15

Family

ID=32991730

Family Applications (2)

Application Number Title Priority Date Filing Date
CH210338D CH210338A (en) 1937-10-05 1938-09-29 Process for the preparation of 2,4-dichloro-6-nitrophenyl-1-trifluoromethylsulfone.
CH211773D CH211773A (en) 1937-10-05 1938-09-29 Process for the preparation of 2,5-dichloro-4-nitrophenyl-1-trifluoromethylsulfone.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CH210338D CH210338A (en) 1937-10-05 1938-09-29 Process for the preparation of 2,4-dichloro-6-nitrophenyl-1-trifluoromethylsulfone.

Country Status (1)

Country Link
CH (2) CH210338A (en)

Also Published As

Publication number Publication date
CH210338A (en) 1940-07-15

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