Allyl bromide → N-Allyl-4-acetamido-3-bromo-2,6-dimethylanisole

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Reaction Conditions

Reaction Steps

Sodium hydride (1.1 g, 27 mmol, 60% dispersion in oil) contained in a round-bottom flask fitted with a reflux condenser was washed using dry hexanes, tetrahydrofuran (50 mL) was added, and the suspension was stirred at 0° C. under a nitrogen atmosphere. A solution of 4-acetamido-3-bromo-2,6-dimethylanisole (7.3 g, 27 mmol) dissolved in tetrahydrofuran (50 mL) was added dropwise using a canulla over about 0.5 h. Allyl bromide (4.85 mL, 84.8 mmoI) was added to the cold solution in one portion, and the mixture was warmed to 60° C. and held there for 17 h. The reaction mixture was quenched with saturated aq. ammonium chloride and extracted with diethyl ether. The combined extracts were washed with brine and dried (MgSO4). Removal of solvents and purification of the resulting viscous liquid by flash column chromatography using 1:3 ethyl acetate:hexanes as eluent gave N-allyl-4-acetamido-3-bromo-2,6-dimethylanisole (8, 8.7 g, 85% yield) as a viscous liquid. Spectral data: 13C NMR: δ 15.2, 16.3, 21.5, 50.1, 59.3, 117.1, 123.3, 129.2, 130.2, 132.37, 132.4, 136.5, 156.2, 169.1; HRMS: calcd. for C14H19BrNO2 (M+H+) 312.0599, fnd. 312.0586.

Provenance & Evidence