Hydrochloric Acid → 5-Methanesulfonyl-2-(2,2,2-trifluoro-ethylsulfanyl)-benzoic acid

HRID 1930979노트

반응식

HRID 1930979 반응식
F[C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[F:21][C:22]([F:26])([F:25])[CH2:23][SH:24].Cl>CN(C)C=O>[CH3:14][S:11]([C:8]1[CH:9]=[CH:10][C:2]([S:24][CH2:23][C:22]([F:26])([F:25])[F:21])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])(=[O:13])=[O:12]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 41339242,2,2-TrifluoroethanethiolHCID 224675662-Fluoro-5-methanesulfonyl-benzoic acid

생성물 1

HCID 211003135-Methanesulfonyl-2-(2,2,2-trifluoro-ethylsulfanyl)-benzoic acid수율 99%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

To a solution of 4.58 mmol 2-fluoro-5-methanesulfonyl-benzoic acid (Example B4(b)) in 6 ml N,N-dimethylformamide were added 13.8 mol cesium carbonate and 9.16 mmol 2,2,2-trifluoro-ethanethiol and the mixture was stirred at 90° C. for 30 min. The reaction mixture was then cooled to room temperature and acidified to pH1 by addition of hydrochloric acid before being extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo to afford the title compound as a red-brown solid which was used in the next step without further purification (yield 99%). MS (m/e): 312.9 ([M−H]−, 100%).

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionbefore being extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-052e3f0867214826a853fb3684f79d99
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188139B2

반응 노트

불러오는 중…