Sodium methanethiolate → 1-Bromo-3-(4-methoxy-benzyloxy)-5-methylsulfanyl-benzene

Participants

Reaction Conditions

Reaction Steps

1,3-Dibromo-5-(4-methoxy-benzyloxy)-benzene (4.0 g) was dissolved in DMF (60 mL), followed by addition of sodium thiomethoxide (829 mg). The resulting mixture was stirred at 75° C. for 5 h. Over the period of 4 hours additional amount of sodium methoxide (total 754 mg) was added in two equal portions. When the starting material was completely consumed the reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified on a silica gel column using ethyl acetate and hexanes to yield the title compound (2.1 g, 60% yield). HRMS calcd for C15H15O2BrS [M+H]+ 339.0049, observed 339.0047.

Provenance & Evidence