Water → 1-Bromoethyl ethyl carbonate
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[Br-:1].[Li+].[C:3](=[O:11])([O:7][CH:8](Cl)[CH3:9])[O:4][CH2:5][CH3:6].O>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.ClCCl>[C:3](=[O:11])([O:7][CH:8]([Br:1])[CH3:9])[O:4][CH2:5][CH3:6][Br-:1].[Li+].[C:3](=[O:11])([O:7][CH:8](Cl)[CH3:9])[O:4][CH2:5][CH3:6].O>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.ClCCl>[C:3](=[O:11])([O:7][CH:8]([Br:1])[CH3:9])[O:4][CH2:5][CH3:6]A mixture of lithium bromide (43 g, 0.5 m), ethyl alphachloroethyl carbonate (15.3 g, 0.1 m); water (100 ml), dichloromethane (100 ml) and cetyl trimethyl ammonium bromide (1.5 g) was stirred at ambient temperature for 24 hours. The aqueous layer was removed and replaced by a fresh solution of lithium bromide (26 g, 0.3 m) in water (40 ml) containing cetyl trimethyl ammonium bromide (1 g). After stirring for a further 24 hours during which time the temperature was raised to 35° C., the organic layer was separated, dried and vacuum distilled to afford after repeated fractionation the new compound, ethyl alpha-bromoethyl carbonate (15.0 g, 76% yield) having a boiling point of 90°-92° C. at 35 mms of mercury pressure.
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