Sulfuric Acid → 5-bromo-6-methoxy-3,4-dihydro-2H-naphthalen-1-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of 6-methoxy-1-tetralone (2.0 g, 11.4 mmol) and NBS (2.0 g, 11.4 mmol) in H2O (30 mL) was added conc. H2SO4 (1.2 mL, 22.7 mmol) at rt. The reaction was stirred at 60° C. for 3 h. The mixture was filtered, and concentrated. Purification by prep-HPLC gave 1.2 g (41%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 2.13-2.18 (2H, m), 2.61 (2H, t, J=6.0 Hz), 3.03 (2H, t, J=6.0 Hz), 3.97 (3H, s), 6.88 (1H, d, J=8.8 Hz), 8.06 (1H, d, J=8.8 Hz). [M+H] Calc'd for C11H11BrO2, 255, 257. Found, 255, 257.

Provenance & Evidence