Benzyl Alcohol → HCID 12985404, compound

Participants

Reaction Conditions

Reaction Steps

Diketene (500 μL, 545 mg, 6.5 mmoles) was dissolved, under nitrogen, in dichloromethane (2 mL), cooled to −25° C., and treated dropwise with a solution of bromine (333 μL, 1.02 g, 6.5 mmoles) in dichloromethane (2 mL). After the addition was complete, the solution was stirred at −25° C. for 15 min, and benzyl alcohol (700 μL, 732 mg, 6.8 mmoles) was added dropwise. Stirring was continued for 15 min, and the solution was warmed to room temperature and evaporated. The residue was dissolved in diethyl ether (20 mL), washed successively with saturated sodium bicarbonate (2×20 mL), water (20 mL) and saturated sodium chloride (20 mL), dried over anhydrous magnesium sulfate and evaporated to give benzyl γ-bromoacetoacetate as a pale yellow oil (1.70 g, 97%). 1HMR (CDCl3, δ): 7.36 (5H, m), 5.19 (2H, s), 4.02 (2H, s), 3.75 (2H, s). IR (neat): 3033, 1734, 1654 cm−1. Mass spectrum (Cl, m/z): 271, 273 (M+1, M+3), Calcd. for C11H11BrO3: C48.69; H 4.05. Found: C 48.55; H 3.94.

Provenance & Evidence