Acetic Acid → 4-Bromo-5-nitroveratrole

Participants

Reaction Conditions

Reaction Steps

Following the procedure of J. Org. Chem. 1960, 25, 721) 4-Bromoveratrole (16.28 g, 75.0 mmol) was slowly added to a stirred solution of concentrated nitric acid (122 ml) and acetic acid (365 ml) maintained at 10° C. The reaction mixture was stirred at 15° C. for one hour, then was diluted with water and extracted with diethyl ether. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was crystallized from ethanol to give 1-bromo-4,5-dimethoxy-2-nitro-benzene (13.144 g, 66.9%) as yellow crystals.

Provenance & Evidence