Methyl chlorodifluoroacetate → HCID 57949784, compound

Participants

Reaction Conditions

Reaction Steps

CuI (0.057 g, 0.3 mmol) and potassium fluoride (0.017 g, 0.3 mmol) were added under N2 atmosphere to a stirred solution of 2-benzyl-7-iodo-2,3-dihydro-isoindol-1-one (0.089 g, 0.25 mmol) and chloro-difluoro-acetic acid methyl ester (0.053 mL, 0.5 mmol) in DMF (3 mL). The mixture was heated at 140° C. for 5-8 h. The reaction was cooled and the solvent evaporated. Silica gel column chromatography of the resulting material using 30% ethyl acetate in hexane afforded 2-benzyl-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.03 g, 41%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.28 (s, 2H), 4.79 (s, 2H), 7.33 (m, 5H), 7.59 (m, 2H), 7.76 (d, 1H). GC-MS: m/z 291 (M)+, 270 (M−20)+.

Provenance & Evidence