2-Bromoethanol → 2-Bromoethyl 3-oxobutanoate

HRID 2418252Notes

Reaction equation

HRID 2418252 reaction equation
[CH2:1]([Br:4])[CH2:2][OH:3].[CH2:5]=[C:6]1[O:10][C:8](=[O:9])[CH2:7]1>C(N(CC)CC)C.ClCCl>[C:8]([O:3][CH2:2][CH2:1][Br:4])(=[O:9])[CH2:7][C:6]([CH3:5])=[O:10]

Participants

5

Reactant 2

HCID 108982-BromoethanolHCID 12661Diketene

Product 1

HCID 132313632-Bromoethyl 3-oxobutanoateYield 90.3%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 30 g of ethylene bromohydrin in ice bath were added by turns 22 g of diketene and 1.5 g of triethylamine with stirring while the reaction temperature was controlled at 30°-40° C. The reaction was continued at room temperature for 3 hours. To the reaction solution was added dichloromethane, the mixture was washed successively with diluted hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution and water and dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was purified by distillation to obtain 45.3 g of 2-bromoethyl acetoacetate.

Workup

  1. customwas controlled at 30°-40° C
  2. washthe mixture was washed successively with diluted hydrochloric acid
  3. dry with materiala saturated aqueous sodium hydrogencarbonate solution and water and dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. distillationthe residue was purified by distillation

Sources & evidence

ORD record
ord-767cc1ead9c74ea4a9451eb868790315
Source dataset
uspto-grants-1984_09
Patent number
US04472411

Reaction notes

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