Triethylamine → 7-bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one

Participants

Reaction Conditions

Reaction Steps

Part 2, Step A: A mixture of 5-bromo-2-iodobenzoic acid (12.6 g, 38.5 mmol), but-3-yn-2-ol (3.1 mL, 2.96 g, 42.4 mmol), ZnCl2 (5.2 g, 38.5 mmol), Pd(Ph3P)4 (2.23 g, 1.9 mmol), Et3N (16.0 mL, 11.7 g, 115.5 mmol) and DMF (80 mL) was stirred under argon at 80° C. for 2 hours. After removal of the volatiles under vacuum, the residue was chromatographed (silica gel, ethyl acetate in hexanes, 0-100%) to provide the intermediate 7-bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one as a brown oil (7.5 g, 72%). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.38-8.45 (1H, m), 7.81 (1H, dd, J=8.35, 2.05 Hz), 7.32 (1H, d, J=8.51 Hz), 6.52-6.59 (1H, m), 4.66 (1H, qd, J=6.52, 0.95 Hz), 1.54-1.60 (3H, m).

Provenance & Evidence