Diethyl [(2-bromophenyl)methylidene]propanedioate → Ethyl 3-(2-bromophenyl)-2-ethoxycarbonyl-3-methylpropionate

HRID 1585968

Reaction equation

HRID 1585968 reaction equation
[CH2:1]([O:3][C:4]([C:6](=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Br:19])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])[CH3:2].[CH3:20][Mg]Br>CCOCC.[Cl-].[NH4+].[Cu](Br)Br>[Br:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH:12]([CH3:20])[CH:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

6

Reactant 2

HCID 246693Diethyl [(2-bromophenyl)methylidene]propanedioateHCID 178418573HCID 178418573, compound

Product 1

HCID 21217382Ethyl 3-(2-bromophenyl)-2-ethoxycarbonyl-3-methylpropionate

Reagents, catalysts & solvents 3

HCID 24611Copper bromide (CuBr2)CatalystHCID 3283Diethyl EtherSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution in 500 ml of ether of 50.98 g of ethyl α-ethoxycarbonyl-o-bromo-cinnamate (170.5 mmole) and 1.0 g of copper bromide was added dropwise 56.7 ml of an ethereal solution of methylmagnesium bromide (175.6 mmole) at -20° C. The mixture was stirred overnight at room temperature, diluted with an aqueous ammonium chloride solution to separate the phases. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure to give ethyl 3-(2-bromophenyl)-2-ethoxycarbonyl-3-methylpropionate.

Workup

  1. customto separate the phases
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-609869689b8d4703b7edca5bf824b63f
Source dataset
uspto-grants-1999_08
Patent number
US05942459

Linked notes

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