Nitric Acid → 2,3,4-Trifluoro-5-nitrobenzoic acid

Participants

Reaction Steps

A 3 liter three neck round bottom flask was charged with 125 ml H2SO4. Fuming nitric acid was added (8.4 ml, 199 mmol) and the mixture gently stirred. 2,3,4-Trifluorobenzoic acid (25 g, 142 mmol) was added in 5 g portions over 90 minutes. The dark brownish yellow solution was stirred for 60 minutes at which time the reaction was complete. The reaction mixture was poured into 1 liter of an ice:water mixture and extracted with diethyl ether (3×600 ml). The combined extracts were dried (MgSO4) and concentrated under reduced pressure to give a yellow solid. The solid was suspended in hexanes and stirred for 30 min after which time it was filtered to give 29 g (92%) of clean desired product as an off-yellow solid: MS APCI (−) m/z 220 (M−1) detected.

Provenance & Evidence