Nitric Acid → HCID 19800071, compound

Participants

Reaction Steps

A solution of 5.12 ml of fuming nitric acid and 4.5 ml of acetic acid was added dropwise, with stirring, to a cooled (5°-10° C.) mixture of 3-bromo-5-fluorobenzo[b]thiophene (5.35 g, 23.15 mmol) and 28.5 ml of acetic anhydride. The reaction mixture was stirred for 2 hours and poured onto ice water (350 ml) and extracted with CH2Cl2 (4×50 ml). The organic phases were combined, washed with water and dried over MgSO4. The solvent was evaporated and the residue was recrystallized from 90% ethanol to yield 1.7 g (26%) of 3-bromo-5-fluoro-2-nitrobenzo[b]thiophene. M.p. 129°-130° C. 1H-NMR(CDCl3): δ7.40 (ddd, 1H), 7.68 (ddd, 1H), 7.78 (dd, 1H).

Provenance & Evidence