Carbon tetrabromide → 2-benzyloxy-5-(2-bromoethyl)-N,N-dimethylbenzamide

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Reaction Steps

To a stirred solution of 2-benzyloxy-5-(2-hydroxyethyl)-N,N-dimethylbenzamide (300 mg) in dichloromethane (5 ml) were added carbon tetrabromide (366 mg) and triphenylphosphine (289 mg) at room temperature, and the mixture was stirred for minutes. After concentration of the reaction mixture under reduced pressure, purification of the residue by flash column chromatography on silica gel (eluent: hexane/ethyl acetate=3/2) gave 2-benzyloxy-5-(2-bromoethyl)-N,N-dimethylbenzamide (124 mg). 1H-NMR(CDCl3) δ ppm: 2.86 (3H, s), 3.00-3.15 (2H, m), 3.11 (3H, s), 3.45-3.60 (2H, m), 5.11 (2H, s), 6.90 (1H, d, J=8.3 Hz), 7.05-7.20 (2H, m), 7.25-7.40 (5H, m)

Provenance & Evidence