Carbon tetrabromide → HCID 18476055, compound

Participants

Reaction Steps

Triphenylphosphine (9.7 g., 37.0 mmol) and then carbon tetrabromide (12.3 g., 37.0 mmol) were added to a stirred solution of methyl 5-hydroxymethyl-2-(4-fluorobenzyl)benzoate (4.6 g., 16.8 mmol) in anhydrous ether (150 ml) at ambient temperature. After 4 hours the reaction was filtered and the filtrate concentrated under reduced pressure. The product was purified by column chromatography eluting with ethyl acetate/isohexane (5:95) to give methyl 5-bromomethyl-2-(4fluorobenzyl)benzoate as a colourless oil (5.05 g). NMR data (CDCl3) δ: 3.83 (3H, s), 4.37 (2H, s), 4.50 (2H, s), 6.92-6.99 (2H, m), 7.06 7.13 (2H, m), 7.19 (1H, d). 7.43 (1H, dd), 7.95 (1H, d).

Provenance & Evidence