Sodium benzenethiolate → 1-[(2E)-4-(4-chlorophenyl)-2,3-difluoro-6-(phenylsulfanyl)-2-hexenyl]-3-phenoxybenzene

HRID 1634381ノート

反応式

HRID 1634381 の反応式
Br[CH2:2][CH2:3][CH:4]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)/[C:5](/[F:22])=[C:6](\[F:21])/[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1.[S-:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[Na+]>C(O)C>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([CH:4]([CH2:3][CH2:2][S:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)/[C:5](/[F:22])=[C:6](\[F:21])/[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=2)=[CH:24][CH:25]=1

参加物

4

反応物 2

HCID 4110039Sodium benzenethiolateHCID 590328721-[(2E)-6-bromo-4-(4-chlorophenyl)-2,3-difluoro-2-hexenyl]-3-phenoxybenzene

生成物 1

HCID 590328761-[(2E)-4-(4-chlorophenyl)-2,3-difluoro-6-(phenylsulfanyl)-2-hexenyl]-3-phenoxybenzene収率 54.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a stirred solution of 1-[(2E)-6-bromo-4-(4-chlorophenyl)-2,3-difluoro-2-hexenyl]-3-phenoxybenzene (0.308 g, 0.64 mmol) in ethanol (9.6 ml) under nitrogen was added sodium thiophenoxide (0.253 g, 1.91 mmol) and the resulting mixture was stirred at room temperature for two hours. The reaction mixture was concentrated in vacuo, diluted with water (25 ml) and extracted with methylene chloride (3×25 ml). The combined organic extracts were washed with water (2×25 ml), dried over anhydrous sodium sulfate and concentrated in vacuo to a colorless oil (0.187 g). Chromatography on a preparative thin layer silica gel plate eluting with ethyl acetate:hexane (5:95) afforded the title compound as a colorless oil (0.176 g) which was characterized by IR, 1HNMR and mass spectral analysis.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with water (25 ml)
  3. extractionextracted with methylene chloride (3×25 ml)
  4. washThe combined organic extracts were washed with water (2×25 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo to a colorless oil (0.187 g)
  7. washChromatography on a preparative thin layer silica gel plate eluting with ethyl acetate:hexane (5:95)

出典と根拠

ORDレコード
ord-c35e072e434043e687d74dc06a7ae8e6
出典データセット
uspto-grants-2003_01
特許番号
US06506800B2

反応ノート

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