Acetic Acid → 6,7-Dibromo-8-nitro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A 20-mL round bottom flask was charged with 6,7-dibromo-2,3-dihydrobenzo[b][1,4]dio-xine-5-carboxylic acid (3.0 g, 0.61 mmol) and acetic acid (2 mL). The mixture was heated to 37° C., following by the addition of a solution of nitric acid (d=1.49, 1.0 mL), acetic acid (1.0 mL) and concentrated sulfuric acid (1.0 mL). After heating at 50° C. for 1 h, the mixture was poured in cold water while stirring. It was then filtered and the solid was washed with water to afforded the title compound (1.91 g, 83%). LCMS: ESI (3 minute run), m/z=382 [M+1]+; Retention time: 1.05 minute.

Provenance & Evidence