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

HRID 225699노트

반응식

HRID 225699 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-7ee2f41ac992435ea69b0e939e3ad1ca
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557114B2

반응 노트

불러오는 중…