Methanol → alpha-(Aminomethyl)-3,4-dichlorobenzenemethanol

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3,4-dichlorobenzaldehyde (3.50 g, 20.2 mmol) and ZnI2 (19 mg, 0.06 mmol) at 0° C. was added TMSCN (2.2 g, 2.2 mmol). The reaction mixture was stirred at 0° C. for 10 min and then warmed to rt and stirred for an additional 1 h. The mixture was concentrated to afford an orange-brown colored oil. The oil was dissolved in THF (20 mL) and BH3.THF (1 M in THF; 25 mL, 25 mmol) was added at 0° C. The reaction mixture was warmed to rt and stirred overnight. The mixture was cooled to 0° C. and MeOH (6 mL) was added with continued stirring for 2 h. After being warmed to rt, the mixture was concentrated. The residue was dissolved in MeOH (10 mL) and HCl (2 M in Et2O; 25 mL) was added at 0° C. After 30 min, Et2O (100 mL) was added and the resulting white solid was filtered and washed with Et2O (2×50 mL) to give a white solid (3.5 g, 72%).

Provenance & Evidence