Sodium Iodide → (5-Bromo-2-chlorophenyl)methanamine

Participants

Reaction Conditions

Reaction Steps

To a solution of chlorotrimethylsilane (3.55 mL, 27.2 mmol) in acetonitrile (70 mL) was added sodium iodide (3.91 g, 27.2 mmol), and the reaction mixture was stirred at −20° C. for 1 h. Then methyl N-[(5-bromo-2-chlorophenyl)methyl]carbamate (3 g, 7.7 mmol; prepared according to U.S. Pat. No. 6,313,071) was added, and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was then basified with 1 N aqueous sodium hydroxide solution and extracted with ethyl acetate (3×). The organic layers were combined, washed with water and brine and then dried (Na2SO4). The solvent was evaporated to provide the title product (1.4 g).

Provenance & Evidence