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

HRID 1634381Notes

Reaction equation

HRID 1634381 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-c35e072e434043e687d74dc06a7ae8e6
Source dataset
uspto-grants-2003_01
Patent number
US06506800B2

Reaction notes

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