Hydrochloric Acid → 3-Bromo-7-methoxy-1-naphthonitrile

Participants

Reaction Conditions

Reaction Steps

To slurry of 3,8-dibromo-7-methoxy-1-naphthonitrile (1.62 kg) and Tin (II) chloride dihydrate (1.24 kg, 5.50 mol) in acetic acid (5 L) is added conc. HCl (37% wt, 2.50 L) through a dropping funnel at 100° C. during a period of 2 h. The mixture is stirred at 100° C. for 4 h. Then, the mixture is cooled to room temperature. The solid is filtered, washed with 1% wt HCl (2×1.00 L), water (1.00 L) and dried to give the title compound as a white solid (524 g, 73%). 1H NMR (CDCl3): δ8.13 (d, 1H, J=1.8 Hz), 7.93 (d, 1H, J=1.9 Hz), 7.72 (d, 1H, J=9.0 Hz),7.41 (d, 1H, J=2.4 Hz), 7.28 (dd, 1H, J=2.4 Hz, 9.0 Hz), 3.99 (s, 3H).

Provenance & Evidence