Bromine → Butyl 3-bromo-2-oxobutanoate

HRID 43615Notes

Reaction equation

HRID 43615 reaction equation
[O:1]=[C:2]([CH2:10][CH3:11])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4].[Br:12]Br>ClCCl>[Br:12][CH:10]([CH3:11])[C:2](=[O:1])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4]

Participants

4

Reactant 2

HCID 24408BromineHCID 54144375HCID 54144375, compound

Product 1

HCID 87440690Butyl 3-bromo-2-oxobutanoateYield 114.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of butyl 2-oxobutanoate (described in Patent; IMPERIAL CHEMICAL INDUSTRIES PLC; Publ.: EP 375457 B1 (1994/03/16), Appl.: EP 1989-313521 (1989/12/22), 14g, 88.6 mmol) in dichloromethane (100 mL) was cooled to 0° C., and bromine (4 mL, 80 mmol) was added over 15 minutes. Following stirring at room temperature for 30 minutes, the reaction solution was washed with aqueous sodium bicarbonate solution, washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 21.8 g of the title compound as a colorless liquid (100%).

Workup

  1. washthe reaction solution was washed with aqueous sodium bicarbonate solution
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d53f9cdd5b974c9bbde8a60fb416a65c
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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