Benzyl Alcohol → HCID 12985404, compound

Temperature

-25 °C

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.

1. additionAfter the addition
2. stirringStirring
3. waitwas continued for 15 min
4. temperaturethe solution was warmed to room temperature
5. customevaporated
6. dissolutionThe residue was dissolved in diethyl ether (20 mL)
7. washwashed successively with saturated sodium bicarbonate (2×20 mL), water (20 mL) and saturated sodium chloride (20 mL)
8. dry with materialdried over anhydrous magnesium sulfate
9. customevaporated

ORD record

ord-afb5a06de86a4babb1a37d59def0a5b3

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06399600B1