N-bromobutanimide → 1-(Benzyloxy)-4-bromo-2-ethyl-5-methoxybenzene

Participants

Reaction Steps

Under a nitrogen atmosphere, 12.60 g (52.00 mmol) of 3-benzyloxy-4-ethyl-1-methoxybenzene (3) and 9.72 g (54.60 mmol) of NBS were combined in 350 mL of carbon tetrachloride, followed by the addition of 50 g of silica gel 60 (EM Science). The reaction was allowed to stir for 16 hours in the absence of light. The reaction mixture was filtered and the silica gel was washed with dichloromethane. The filtrate was washed with ethyl acetate (1×300 mL). The combined organic extracts were washed with 1M NaOH (2×300 mL), dilute NaHSO3 (1×200 mL) and brine (1×200 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to yield 16.82 g (100%) of crude, 5-benzyloxy-2-bromo-4-ethyl-1-methoxybenzene (4) as a colorless oil.

Provenance & Evidence