Potassium ethanethioate → ethanethioic acid S-[3,3-difluoro-3-(4-fluorophenyl)-propyl]ester

HRID 925261ノート

反応式

HRID 925261 の反応式
Br[CH2:2][CH2:3][C:4]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)([F:6])[F:5].[C:14]([O-:17])(=[S:16])[CH3:15].[K+]>CN(C=O)C.O>[F:5][C:4]([F:6])([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)[CH2:3][CH2:2][S:16][C:14](=[O:17])[CH3:15]

参加物

5

反応物 2

HCID 23670855Potassium ethanethioateHCID 671338221-(3-Bromo-1,1-difluoropropyl)-4-fluorobenzene

生成物 1

HCID 86720161ethanethioic acid S-[3,3-difluoro-3-(4-fluorophenyl)-propyl]ester収率 88%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of 1-(3-bromo-1,1-difluoro-propyl)-4-fluoro-benzene (synthesized according to the methods described in sections a) to e) of example 1) (0.25 g, 1.2 mmol) in dry DMF (1 ml) is added potassium thioacetate (0.41 g, 3.60 mmol) at RT. The reaction mixture is heated at 60° C. for 1.5 h. After completion of the reaction, the mixture is diluted with water (30 ml) and extracted with EtOAc (3×30 ml). The organic layer is washed with water (30 ml), brine (30 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 1% EtOAc/hexane) to yield ethanethioic acid S-[3,3-difluoro-3-(4-fluorophenyl)-propyl]ester (0.26 g, 1.05 mmol, 88%).

後処理

  1. customAfter completion of the reaction
  2. extractionextracted with EtOAc (3×30 ml)
  3. washThe organic layer is washed with water (30 ml), brine (30 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customto get the crude product, which
  7. customis purified by column chromatography (silica gel, 1% EtOAc/hexane)

出典と根拠

ORDレコード
ord-db16b47a487c4aed93dad8f16ce197bf
出典データセット
uspto-grants-2016_03
特許番号
US09284286B2

反応ノート

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