Benzyl Bromide → HCID 14499222, compound

Participants

Reaction Steps

The oil was removed from 100 mg (50% in oil, 2.1 mmol, Alfa) of sodium hydride dispersion by washing with three portions of petroleum ether then the residue was covered with 10 ml of dry THF. A total of 530 mg (2.00 mmol) of 4-[(6-methoxy-2-naphthyl)amino]phenol (prepared as described in Example 2) was added to the resulting mixture in several portions. The deep purple reaction mixture was stirred for an additional 10 minutes until hydrogen evolution ceased then 1 ml of sieve-dried DMF was added, followed by 240 ul (2.02 mmol, Aldrich) of benzyl bromide. The solution was heated to 50° for 1 hour, cooled, added to 50 ml of H2O and extracted with 50 ml of ethyl acetate. The organic extract was washed with two additional portions of H2O, dried (MgSO4) and concentrated in vacuo to give 690 mg (97%) of crude title compound as a lavender solid, m.p. 155°-157°.

Provenance & Evidence