Lithium Chloride → Ethyl 3-(2-bromophenyl)-3-methylpropionate

HRID 1585969Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:20])[CH:9](C(OCC)=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11].[Cl-].[Li+]>CS(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:20])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 52.96 g the crude ethyl 3-(2-bromophenyl)-2-ethoxycarbonyl-3-methylpropionate (168.13 mmole) in dimethylsulfoxide (250 ml) and water (3 ml) was added 14 g of lithium chloride, and the mixture was heated at 150° C. for 2.5 hours. After cooling the mixture, dimethylsulfoxide was removed under reduced pressure, and the residue was diluted with an aqueous sodium chloride solution and extracted with ethyl acetate. The organic phase was washed with an aqueous ammonium chloride solution and dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residual concentrate was further purified by distillation to give 28.04 g of ethyl 3-(2-bromophenyl)-3-methylpropionate (65%).

Workup

customwas removed under reduced pressure
additionthe residue was diluted with an aqueous sodium chloride solution
extractionextracted with ethyl acetate
washThe organic phase was washed with an aqueous ammonium chloride solution
dry with materialdried over magnesium sulfate
customthe solvent was removed under reduced pressure
concentrationThe residual concentrate
distillationwas further purified by distillation

Sources & evidence

ORD record: ord-c28d13d9d3014529ae59ac1d18a80002
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05942459

Reaction notes

Loading…