Styrene → 3-Bromo5-styryl-benzaldehyde

HRID 984347Notes

Reaction equation

HRID 984347 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([Br:24])[CH:23]=1)[CH:19]=[O:20]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:24][C:22]1[CH:21]=[C:18]([CH:17]=[C:16]([CH:1]=[CH:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:23]=1)[CH:19]=[O:20]

Participants

7

Reactant 3

HCID 7501StyreneHCID 11430Potassium CarbonateHCID 6220773,5-Dibromobenzaldehyde

Product 1

HCID 739917743-Bromo5-styryl-benzaldehydeYield 31.3%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of styrene (2.0 g, 18.9 mmol), potassium carbonate (7.8 g, 56.7 mmol), tetra-N-butylammonium bromide (2.0 g, 6.3 mmol) and palladium(II) acetate (250 mg, 1.11 mmol), under nitrogen, was stirred for 10 min. A solution of 3,5-dibromobenzaldehyde (5.0 g, 18.9 mmol) in dry DMF (10 mL) was added and the mixture heated at 65° C. for 16 h. The reaction mixture was concentrated in vacuo, and the product purified by flash chromatography (heptane/ethyl acetate 1:4) to give 1.7 g of 3-bromo-5-styryl-benzaldehyde.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe product purified by flash chromatography (heptane/ethyl acetate 1:4)

Sources & evidence

ORD record
ord-3736678def7e46be84d7d47ecad937e3
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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