Water → 4-Bromo-7-fluoro-1,2-dihydroisoquinolin-1-one

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Reaction Conditions

Reaction Steps

Bromine (3.8 g, 24 mmol) in acetic acid (6 mL) was added slowly to a mixture of 7-fluoro-2-methylisoquinolin-1-one (4 g, 22.4 mmol) in acetic acid (8 mL) at 0° C. After stirring at 26° C. for 2 h, the mixture was poured into water (100 mL) and the solid was collected by filtration. Purification by silica gel chromatography (PE:EA=20:1) gave the title compound (1.4 g, 44%) as an off-white solid. 1H NMR (CDCl3, 400 MHz) δ 8.11 (d, J=9.2 Hz, 1H), 7.84 (dd, J1=9.6 Hz, J2=4.8 Hz, 1H), 7.49-7.45 (m, 1H), 7.34 (s, 1H), 3.62 (3H, s). LCMS: 255.9 [M+H]+

Provenance & Evidence