Lithium Bromide → 1-Bromoethyl ethyl carbonate

HRID 620448Notes

Reaction equation

HRID 620448 reaction equation
[Br-:1].[Li+].[C:3](=[O:11])([O:7][CH:8](Cl)[CH3:9])[O:4][CH2:5][CH3:6]>CN(C)C=O>[C:3](=[O:11])([O:7][CH:8]([Br:1])[CH3:9])[O:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 162095Carbonic acid, 1-chloroethyl ethyl ester

Product 1

HCID 30215501-Bromoethyl ethyl carbonateYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Lithium bromide (17.4 g, 0.2 m) was dissolved in dimethyl formamide (150 ml) and the mixture cooled to ambient temperature. Ethyl alphachloroethyl carbonate (30.5 g, 0.2 m) was added and the mixture stirred at ambient temperature for 24 hours. The precipitated lithium chloride was filtered off and the filtrate vacuum distilled to afford after careful re-fractionation, ethyl alpha-bromoethyl carbonate in 76% yield based upon recovered ethyl alphachloroethyl carbonate.

Workup

  1. filtrationThe precipitated lithium chloride was filtered off
  2. distillationthe filtrate vacuum distilled

Sources & evidence

ORD record
ord-1cfbe2be57114f33812c3c9bb4db9c5b
Source dataset
uspto-grants-1989_04
Patent number
US04820857

Reaction notes

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