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

HRID 1634381노트

반응식

HRID 1634381 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c35e072e434043e687d74dc06a7ae8e6
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506800B2

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