HCID 67403247, compound → HCID 67402411, compound

Participants

Reaction Steps

A mixture of methyl 4-iodo-5-nitro-2-(trifluoromethyl)benzoate (desired) and methyl 4-iodo-3-nitro-2-(trifluoromethyl)benzoate as obtained in step 3 (1.7 g, 4.53 mmol) in acetic acid (20 mL) was treated with iron powder (1.5 g, 26.8 mmol) at 45° C. for 2 h. The reaction mixture was cooled to ambient temperature and was filtered through celite. The filter cake was washed with ethyl acetate and the filtrate was concentrated. The residue was diluted with ethyl acetate, washed with saturated sodium bicarbonate and brine, dried over sodium sulfate, then filtered and concentrated to afford a brown oil which was purified by column chromatography (silica gel, 10-30% ethyl acetate in hexanes) to afford the two regioisomers methyl 5-amino-4-iodo-2-(trifluoromethyl)benzoate (major) and methyl 3-amino-4-iodo-2-(trifluoromethyl)benzoate (minor) in a 4:1 ratio (1.484 g, 4.30 mmol, 95% yield). 1H NMR for desired (major) isomer (400 MHz, CDCl3): δ 7.96 (s, 1H), 7.06 (s, 1H), 4.55 (br s, 2H), 3.90 (s, 3H); GCMS for C9H7F31NO2: 345 (M+).

Provenance & Evidence