Oxygen → Ethyl 4-bromo-3-oxobutanoate

To a solution of 3-oxo-butyric acid ethyl ester (10.0 g, 78 mmol) in 100 mL of chloroform was added bromine (2.02 mL, 78 mmol) dropwise. The solution was stirred at room temperature for 60 hours without capping the flask (extended stirring at room temperature in an open system with oxygen flow facilitated the bromine migration from C-2 to C-4). The reaction mixture was partitioned between chloroform and water and the organic phase was dried over sodium sulfate. The organic solution was concentrated to provide 4-bromo-3-oxo-butyric acid ethyl ester (12.5 g, 45%). The crude product was taken on to the next step without further purification.

1. customThe reaction mixture was partitioned between chloroform and water
2. dry with materialthe organic phase was dried over sodium sulfate
3. concentrationThe organic solution was concentrated

ORD record

ord-e16a57fc1cc2404dbab7b14c34e22d20

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609680B2