Nitric Acid → 2,6-Difluoro-3-nitrotoluene

Participants

Reaction Steps

A solution of 1,3-difluoro-2-methylbenzene (15 g, 0.12 mol) in H2SO4 (100 mL) was treated dropwise with HNO3 (65%, 11.4 g, 0.12 mol) at −10° C. The resultant mixture was stirred for about 30 min. The mixture was poured into ice-water and extracted with EtOAc (3×200 mL). The combined organics were washed with brine, dried (NaSO4) and concentrated in vacuo to give 1,3-difluoro-2-methyl-4-nitrobenzene (16 g, 78% yield). 1H NMR (400 MHz, CDCl3) δ 7.80 (m, 1H), 6.8-7.1 (m, 1H), 2.30 (s, 3H).

Provenance & Evidence