1,1-Dichloroethane → Acetic acid, 2-[(3-bromophenyl)sulfonyl]-, methyl ester

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Reaction Steps

A solution of 6.0 g (23 mmol) of (3-bromo-phenylsulfanyl)-acetic acid methyl ester in 50 mL of dichloroethane was treated with 6.2 g (25 mmol) of 3-chloroperbenzoic acid. After 30 min of stirring another 6.2 g (25 mmol) of 3-chloroperbenzoic acid were added, the resulting suspension was stirred overnight at RT and then treated with a 0.5 M aqueous solution of sodium thiosulfate. The phases were separated and the aqueous one extracted twice with diethylether. The combined organic phases were washed with a ca. 1M aqueous NaHCO3 solution, dried over Na2SO4, filtered and evaporated to give 6.3 g (93%) of (3-bromo-benzenesulfonyl)-acetic acid methyl ester as a colorless oil, MS: 312 (MNH4+, 1Br).

Provenance & Evidence