Benzyltrimethylammonium hydroxide → (Z)-N-(4-chlorophenethyl)-4-(2-bromo-4-(2-(methylsulfinyl)-2-(methylthio)vinyl)phenoxy)benzamide

Participants

Reaction Conditions

Reaction Steps

N-(4-chlorophenethyl)-4-(2-bromo-4-formylphenoxy)benzamide (1.6 g, 3.5 mmol) was diluted with THF (10 mL) followed by the addition of N,N,N-trimethyl(phenyl)methanaminium hydroxide (0.79 ml, 1.7 mmol) and methylsulfinyl (methylthio)methane (0.87 g, 7.0 mmol). The reaction was stirred at 70° C. for 2 hours. The reaction mixture was loaded directly onto a silica gel column and eluted with DCM:MeOH (98:2) to yield (Z)—N-(4-chlorophenethyl)-4-(2-bromo-4-(2-(methylsulfinyl)-2-(methylthio) vinyl)phenoxy)benzamide (1.9 g, 96% yield).

Provenance & Evidence