Nitric Acid → 4-Bromo-5-nitroveratrole

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Reaction Steps

4-Bromoveratrole (50 g, 0.23 mol) was added dropwise at 6°-9° to a stirred solution of 175 ml of concentrated nitric acid and glacial acetic acid (525 ml). After stirring at 6°-11° for 1.5 hours, the mixture was poured into 2.5 liters of ice-water. The light yellow solid was filtered after 0.5 hour, washed with water, and air-dried (62.5 g); m.p. 120°-122° (s. 118°). Following crystallization from 400 ml of ethanol, the title A compound as a light yellow product weighed 50.0 g; m.p. 121°-123°. Lit. m.p. 120°-122°, 122°-124° (J. Org. Chem., 25, 724 (1960).

Provenance & Evidence