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

HRID 1352265ノート

反応式

HRID 1352265 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of 4.58 mmol 2-fluoro-5-methanesulfonyl-benzoic acid (Example A14(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%).

後処理

  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

出典と根拠

ORDレコード
ord-ffda3c5b4ec74d39a962a492c605ada5
出典データセット
uspto-grants-2007_05
特許番号
US07220744B2

反応ノート

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