Methanol → 1-Bromo-3-(1-[4-methanesulfonyl-phenyl]-vinyl)-benzene

HRID 1668759Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13](SC)=[CH:12][CH:11]=2)=[CH2:9])[CH:3]=1.O[O:19][S:20]([O-:22])=O.[K+].[CH3:24]O>O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([C:10]2[CH:11]=[CH:12][C:13]([S:20]([CH3:24])(=[O:22])=[O:19])=[CH:14][CH:15]=2)=[CH2:9])[CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 1-bromo-3-(1-[4-methylsulfanyl-phenyl]-vinyl)-benzene (0.5 g, 0.16 mmol, 1 eq) in methanol (15 mL) was added over 5 min Oxone® (2.0 g, 0.32 mmol, 2.0 eq) dissolved in water (15 mL). After stirring at 25° C. for 2 h, the reaction mixture was diluted with water (40 mL) and extracted with dichloromethane (3×40 mL). The organic layer was washed with brine (20 mL) and dried on magnesium sulfate. After filtration and concentration, the crude material was chromatographed (silica gel: cyclohexane/ethyl acetate, 4:1) to give an oil (0.3 g, 56% yield).

Workup

extractionextracted with dichloromethane (3×40 mL)
washThe organic layer was washed with brine (20 mL)
customdried on magnesium sulfate
filtrationAfter filtration and concentration
customthe crude material was chromatographed (silica gel: cyclohexane/ethyl acetate, 4:1)

Sources & evidence

ORD record: ord-c806076faeee466e81d6c49b5b3240a3
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989449B2

Reaction notes

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