3-(Trifluoromethyl)benzoyl chloride → 8-nitro-2-(3-(trifluoromethyl)phenyl)-4H-chromen-4-one

Participants

Reaction Conditions

Reaction Steps

1-(2-Hydroxy-3-nitrophenyl)ethanone 1 (1.2 g, 6.61 mmol) was taken up in 20 mL of pyridine along with 3-trifluoromethylbenzoyl chloride 48 (1.2 mL, 7.9 mmol) and DBU (2.9 mL, 14.5 mmol). The reaction mixture was stirred at 80° C. for 18 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was diluted with EtOAc and washed with dilute 1 N HCl. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Purification by chromatography (1:1 pentane/EtOAc) afforded 300 mg of 2. MS (ESI) calcd for C16H8F3NO4: 335.04. found: 336 [M+H].

Provenance & Evidence