Chlorosuccinimide → 1-Chloro-2-methoxy-6-(4-methoxyphenyl)naphthalene

Participants

Reaction Steps

A suspension of 2-methoxy-6-(4-methoxyphenyl)naphthalene (0.51 g, 1.93 mmol) and NCS (0.28 g, 2.13 mmol) in acetonitrile (20 mL) was heated to reflux for 3 hr. The resulting solution was cooled to room temperature and the resulting solid was collected by filtration and rinsed with acetonitrile to yield 0.41 g (72%) of the title compound as a white solid: mp 158–164° C.; 1H NMR (CDCl3): δ 3.87 (3H, s), 4.05 (3H, s), 7.03 (2H, d, J=8.62 Hz), 7.32 (1H, d, J=9.02 Hz); 7.65 (2H, d, J=8.55 Hz), 7.82 (2H, d, J=9.01 Hz), 7.95 (1H, d, J=1.36 Hz), 8.27 (1H, d, J=8.81 Hz); MS (El) m/z 298 (M)+.

Provenance & Evidence