Iodine → HCID 19935801, compound

Participants

Reaction Steps

To a solution of 1-bromo-3,5-difluorobenzene (10 g, 57.14 mmol) in dry tetrahydrofuran (60 mL), under nitrogen, was added magnesium turnings (1.37 g, 57.14 mmol) and one crystal of Iodine. The mixture started to reflux spontaneously and when all magnesium was consumed, a solution of 1-benzylpyrrolidin-3-one (10 g, 57.14 mmol) in dry tetrahydrofuran (40 mL) was added drop wise. The resulting mixture was heated to 60° C. for 2 h after which aqueous saturated ammonium chloride solution (50 mL) was added. The mixture was extracted with ethyl acetate (2×50 mL) and the combined organic phase was dried (Na2SO4) and evaporated. Purification twice by flash chromatography on silica gel (isooctane/ethyl acetate, 1:1 and 6:4) gave the title compound (5.5 g). MS m/z (rel. intensity, 70 eV) 289 (M+, 9), 198 (61), 133 (51), 132 (41), 91 (bp).

Provenance & Evidence