Carbon tetrabromide → 3-Methoxy-4-nitrobenzyl bromide

Participants

Reaction Steps

Carbon tetrabromide (0.543 g, 1.638 mmol) and triphenylphosphine (0.430 g, 1.638 mmol) were added to a solution of (3-methoxy-4-nitrophenyl)methanol (0.2 g, 1.092 mmol) in THF (5.46 mL). The reaction mixture was stirred at room temperature overnight before being concentrated under reduced pressure and purified via Biotage silica gel column chromatography eluting with (cyclohexane/EtOAc 99/1 to 80/20) to afford the title product as a yellow solid (220 mg, 82%). 1H NMR (500 MHz, CDCl3): δ 4.00 (s, 3H), 4.48 (s, 2H), 7.06 (dd, J=8.3, 1.7 Hz, 1H), 7.12 (d, J=1.7 Hz, 1H), 7.84 (d, J=8.3 Hz, 1H)

Provenance & Evidence