Carbon Dioxide → 4-Chloro-2-fluoro-3-(methylthio)benzoic acid

HRID 341742

반응식

HRID 341742 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[S:9][CH3:10].[C:11](=[O:13])=[O:12]>CCCCCC.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]([OH:13])=[O:12])=[C:4]([F:8])[C:3]=1[S:9][CH3:10]

참가 물질

5

반응물 2

HCID 280Carbon DioxideHCID 53633719(2-Chloro-6-fluorophenyl)(methyl)sulfane

생성물 1

HCID 541320414-Chloro-2-fluoro-3-(methylthio)benzoic acid

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

n-Butylithium (2.5M in hexane, 140 ml) was added to a stirred, cooled solution of crude 2-chloro-6-fluorothioanisole (60.0 g) in dry tetrahydrofuran while maintaining the temperature below -70° C. The mixture was stirred at -78° C. for 3.5 hours then poured onto solid carbon dioxide pellets. It was stirred and allowed to warm to room temperature. It was evaporated to dryness and the residue was dissolved in water and washed with ether. The aqueous layer was acidified to pH1 and extracted with ether, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with hexane and filtered to give 4-chloro-2-fluoro-3-(methylsulphenyl)benzoic acid as a white solid, m.p. 183°-185° C.

후처리

  1. temperaturewhile maintaining the temperature below -70° C
  2. stirringIt was stirred
  3. temperatureto warm to room temperature
  4. customIt was evaporated to dryness
  5. dissolutionthe residue was dissolved in water
  6. washwashed with ether
  7. extractionextracted with ether
  8. washwashed with water
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customThe filtrate was evaporated to dryness
  12. customthe residue was triturated with hexane
  13. filtrationfiltered

출처 및 근거

ORD 기록
ord-34596e180732413fa4e5a6f09c5b0398
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856274

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