Methanol → 1-(Bromomethyl)-2-methanesulfonylbenzene
Reaction equation
CS[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][Br:6].O[O:12][S:13]([O-:15])=O.[K+].[CH3:17]O>O>[CH3:17][S:13]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][Br:6])(=[O:15])=[O:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 124 mg (0.57 mmol) of 2-(methylthio)-benzylbromide in 8.0 mL of methanol was added a solution of 702 mg of oxone in 7.0 mL of water. The solution was stirred for 4.5 h, concentrated in vacuo and purified by silica gel flash chromatography, eluting with 10% ethyl acetate/hexane to give 105 mg of the title compound. mass spec 249(M+). NMR (CDCl3): δ 3.25 (s, 3H), 5.07 (s, 2H), 7.50 (m, 1H), 7.60 (m, 2H), 8.05 (d, 1H).
Workup
- concentrationconcentrated in vacuo
- custompurified by silica gel flash chromatography
- washeluting with 10% ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-11363b0229f34597bd9f6f342ba64980
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05750549
Reaction notes
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