Carbon tetrabromide → 3-Methoxy-4-nitrobenzyl bromide

Participants

Reaction Conditions

Reaction Steps

To a 250 mL round bottomed flask containing 10 g (54.6 mmol) of 4-nitro-3-methoxybenzyl alcohol in 30 mL THF was added, 36 g (109 mmol, 2 eq.) of carbon tetrabromide followed by 15.9 g (60 mmol, 1.1 eq.) triphenylphosphine at 0° C. The mixture was stirred at 0° C. for 3 hours. Upon removal of the solvent, the residue was purified by flash chromatography, eluting with 10:90 EtOAc-Hexane, to give 11 g (82%) of the product as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.86 (s, 1H), 7.84 (m, 1H), 7.12 (s, 1H), 7.07 (m, 1H), 4.47 (s, 2H), 4.00 (s, 3H).

Provenance & Evidence