Water → 1-Bromo-3-(methylthio)-5-(phenylmethoxy)benzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-benzyloxy-3,5-dibromo-benzene (9.6 g, 28.1 mmol) in dry DMF (55 mL) was added sodium thiomethoxide (1.97 g, 28.1 mmol). The reaction mixture was then stirred at 100° C. for 1 h. After cooling to room temperature, the reaction mixture was poured into a mixture of diethyl ether (50 mL) and water (20 mL) along with intense stirring. The organic layer was separated and washed with water and brine. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica using hexanes-acetone (5:0.2) as eluent to afford 3.68 g (42%) of title compound as an yellow oil. 1H NMR (CDCl3, 300 MHz): δ 7.41-7.26 (m, 5H); 6.96 (s, 1H); 6.90 (s, 1H); 6.80 (s, 1H); 5.05 (s, 2H); 2.46 (s, 3H).

Provenance & Evidence