m-Chloroperbenzoic acid → 1-[2'-Chlorophenylsulphinyl]-2-phenyl-2-propene

HRID 2372649Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH2:11].C1C=C(Cl)C=C(C(OO)=[O:26])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH2:9][C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[CH2:11])=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

1-[2'-Chlorophenylthio]-2-phenyl-2-propene (1.56 g, 0.006 mole) is dissolved in methylene chloride (50 cc) and cooled to 0° C. 55% strength mCPBA (1.9 g, 0.006 mole) in solution in methylene chloride (15 cc) is added dropwise over 30 min. After 1 hour at 0° C. the solution is washed with saturated sodium bicarbonate (75 cc), brine (2×75 cc) and is dried over MgSO4. The crude (1.6 g) is chromatographed on silica to give 1-[2'-chlorophenylsulphinyl]-2-phenyl-2-propene (1.0 g, 60%) in the form of an oil. nD25 =1.6250.

Workup

washAfter 1 hour at 0° C. the solution is washed with saturated sodium bicarbonate (75 cc), brine (2×75 cc)
dry with materialis dried over MgSO4
customThe crude (1.6 g) is chromatographed on silica

Sources & evidence

ORD record: ord-3c1b20a861d8406d994db7afd29ccddb
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05100460

Reaction notes

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