Benzyl Bromide → HCID 58292748, compound

Participants

Reaction Steps

To a solution of 2-bromo-6-hydroxy-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (3.00 g, 10.0 mmol) in DMF (20 mL) was added K2CO3 (2.76 g, 20.0 mmol) followed by benzyl bromide (1.43 mL, 12.0 mmol) at 0° C. The suspension was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was separated, dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=6:1) to give the title compound (3.79 g, 97%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 10.39 (s, 1H), 7.47-7.33 (m, 5H), 6.98 (d, J=2.1 Hz, 1H), 6.70 (d, J=2.1 Hz, 1H), 5.47-5.45 (m, 1H), 5.16 (s, 2H), 3.80-3.78 (m, 1H), 3.66-3.62 (m, 1H), 1.88-1.55 (m, 6H).

Provenance & Evidence