Water → Ethyl 3-(2-bromophenyl)-2-methylpropionate

HRID 1585972Notes

Reaction equation

HRID 1585972 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][C:5](C)([C:11](OCC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[Cl-].[Li+].O>CS(C)=O>[Br:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][CH:5]([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 21217385Diethyl 2-(2-bromobenzyl)-2-methylmalonate

Product 1

HCID 21217380Ethyl 3-(2-bromophenyl)-2-methylpropionateYield 100.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of diethyl 2-(2-bromobenzyl)-2-methylmalonate (108 g, 310 mmole) in dimethylsulfoxide (350 ml) were added 26.4 g of lithium chloride (620 mmole) and 5.6 ml of water (310 mmole). After stirring at 180° C. for 8 hours, the product was extracted with n-hexane and concentrated to give 84.1 g of ethyl 3-(2-bromophenyl)-2-methylpropionate as a yellow oil (yield, 100%).

Workup

  1. extractionthe product was extracted with n-hexane
  2. concentrationconcentrated
  3. customto give

Sources & evidence

ORD record
ord-8d3aa1d4cc0c4858b4e0abb7a6c4038e
Source dataset
uspto-grants-1999_08
Patent number
US05942459

Reaction notes

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