Methyl chlorodifluoroacetate → HCID 67251332, compound

Participants

Reaction Conditions

Reaction Steps

CuI (0.080 g, 0.42 mmol) and potassium fluoride (0.024 g, 0.42 mmol) were added under an N2 atmosphere to a solution 5-chloro-2-cyclopropyl methyl-7-iodo-2,3-dihydro-isoindol-1-one (0.123 g, 0.35 mmol) and chloro-difluoro-acetic acid methyl ester (0.046 mL, 0.42 mmol) in DMF (4 mL). The mixture was stirred at 140° C. for 18 h. The reaction was cooled and the solvent evaporated. Silica gel column chromatography using 30% ethyl acetate in hexane afforded 5-chloro-2-cyclopropyl methyl-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.020 g, 20%). 1H NMR (300 MHz, CDCl3): δ (ppm) 0.33 (s, 2H), 0.59 (m, 2H), 1.05 (m, 1H), 3.48 (d, 2H) 4.53 (s, 2H), 7.64 (s, 1H), 7.73 (s, 1H). GC-MS: m/z 289 (M)+, 274 (M-15)+.

Provenance & Evidence