Methyl chlorodifluoroacetate → HCID 57949628, compound

Participants

Reaction Conditions

Reaction Steps

CuI (0.076 g, 0.4 mmol) and potassium fluoride (0.023 g, 0.4 mmol) were added under an N2 atmosphere to a solution 5-chloro-2-(4-fluoro-benzyl)-7-iodo-2,3-dihydro-isoindol-1-one (0.149 g, 0.37 mmol) and chloro-difluoro-acetic acid methyl ester (0.046 mL, 0.43 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-fluoro-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.025 g, 20%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.37 (s, 2H), 4.76 (s, 2H) 7.05 (m, 2H), 7.26 (m, 2H), 7.56 (s, 1H), 7.78 (s, 1H). GC-MS: m/z 343 (M)+, 322 (M−21)+.

Provenance & Evidence