Thionyl Chloride → 4-Bromo-N-(2-chloroethyl)-N-methylbenzenemethanamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 72 (2.9 g, 11.9 mmol) in toluene (20 ml) at RT was added SOCl2 (2.83 g, 2 eq, 23.8 mmol) and the mixture was heated to 60° C. for 3 hrs. The solvent was removed and the crude was dissolved in EtOAc then partitioned between water and satd NaHCO3 soln. The organic phase was collected, dried over Na2SO4, filtered and concentrated. The crude was purified by column chromatography (20% EtOAc in hexane) to afford 73 as a brown oil (2.9 g, 93% yield). 1H NMR (DMSO-d6) δ (ppm): 7.45 (m, 2H), 7.21 (m, 2H), 3.57 (t, J=6.85 Hz, 2H), 3.52 (s, 2H), 2.74 (t, J=6.85 Hz, 2H), 2.26 (s, 3H).

Provenance & Evidence