Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → methyl(E)-3-(4-bromo-3-methylphenyl)acrylate

HRID 250860Notes

Reaction equation

HRID 250860 reaction equation
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][C:27]=1[CH3:34]>C1(C)C=CC=CC=1>[Br:25][C:26]1[CH:33]=[CH:32][C:29](/[CH:30]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[CH:28][C:27]=1[CH3:34]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 109215214-Bromo-3-methylbenzaldehyde

Product 1

HCID 67272241methyl(E)-3-(4-bromo-3-methylphenyl)acrylateYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

2.1 g (6.45 mmol, 1.5 eq) of methyl triphenylphosphoranylideneacetate are added to a solution of 900 mg of 4-bromo-3-methylbenzaldehyde in 5 ml of toluene. The reaction mixture is heated at 90° C. for 1 hour. The solvent is evaporated off and the residual oil is chromatographed on silica gel (8/2 heptane/ethyl acetate). 610 mg of methyl (E)-3-(4-bromo-3-methylphenyl)acrylate are obtained in oil form. Yield=55% over steps a, b and c.

Workup

  1. customThe solvent is evaporated off
  2. customthe residual oil is chromatographed on silica gel (8/2 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-2e8395febb2845dea37d7b8ff4862904
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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