Nitric Acid → 4,5-Difluoro-2-nitrophenol

Participants

Reaction Steps

A solution of 3,4-difluorophenol (5.0 g, 38.4 mmol) and tetrabutylammonium bromide (1.239 g, 3.8 mmol) in dichloroethane (30 mL) were added into a 250 mL round-bottomed flask. The mixture was stirred for 45 min before nitric acid (86 g, 96.09 mmol) (7%) was added. The reaction was stirred at RT for 14 h. Water (100 mL) and DCM (50 mL) was added. After stirring for another 10 min, the mixture was partitioned, and the aqueous layer was extracted with DCM (1×20 mL). The combined organic layer was dried (Na2SO4), and concentrated to give the crude product. The crude product was purified by chromatography on silica gel using EtOAc/hexance (0-50%, 30 min). Collected fractions were concentrated to give the title product (2.0 g, 30% yield).

Provenance & Evidence