m-Chloroperbenzoic acid → (4E)-3-(4-chlorophenyl)-4,5-difluoro-6-(3-phenoxyphenyl)-4-hexenyl phenyl sulfoxide

HRID 1634382Notes

Reaction equation

HRID 1634382 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:27][CH2:28][S:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)/[C:9](/[F:26])=[C:10](\[F:25])/[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:44])C=1>C(Cl)Cl>[C:30]1([S:29]([CH2:28][CH2:27][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)/[C:9](/[F:26])=[C:10](\[F:25])/[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)=[O:44])[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 590328761-[(2E)-4-(4-chlorophenyl)-2,3-difluoro-6-(phenylsulfanyl)-2-hexenyl]-3-phenoxybenzene

Product 1

HCID 59032877(4E)-3-(4-chlorophenyl)-4,5-difluoro-6-(3-phenoxyphenyl)-4-hexenyl phenyl sulfoxideYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of 1-[(2E)-4-(4-chlorophenyl)-2,3-difluoro-6-(phenylsulfanyl)-2-hexenyl]-3-phenoxybenzene (0.311 g, 0.61 mmol) in methylene chloride (13 ml) under nitrogen was added dropwise a solution of m-chloroperbenzoic acid (m-CPBA; 0.13 g, 0.65 mmol) in methylene chloride (2 ml) over one minute. The reaction mixture was stirred at room temperature for two hours, diluted with methylene chloride (50 ml) and washed successively with saturated aqueous sodium bicarbonate and water. The organic solution was dried over anhydrous sodium sulfate and concentrated in vacuo to afford the title compound as a colorless syrup (0.318 g), which was characterized by IR, 1HNMR, 19FNMR and mass spectral analysis, and used without further purification.

Workup

  1. washwashed successively with saturated aqueous sodium bicarbonate and water
  2. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a92c1c07973949f596b6c978ee889c54
Source dataset
uspto-grants-2003_01
Patent number
US06506800B2

Reaction notes

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