Methyl chlorodifluoroacetate → HCID 57949698, compound

Participants

Reaction Conditions

Reaction Steps

CuI (0.076 g, 0.4 mmol) and potassium fluoride (0.055 g, 0.29 mmol) were added under an N2 atmosphere to a solution 5-chloro-2-(4-methoxy-benzyl)-7-iodo-2,3-dihydro-isoindol-1-one (0.100 g, 0.24 mmol) and chloro-difluoro-acetic acid methyl ester (0.031 mL, 0.29 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-(4-methoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.042 g, 50%). 1H NMR (300 MHz, CDCl3): δ (ppm) 3.79 (s, 3H), 4.25 (s, 2H), 4.72 (s, 2H) 6.86 (d, 2H), 7.25 (d, 2H), 7.56 (s, 1H), 7.73 (s, 1H). GC-MS: m/z 355 (M)+, 334 (M−21)+.

Provenance & Evidence