3,5-Dibromostyrene → 3,5-Dibromoethylbenzene

HRID 1822316Notes

Reaction equation

HRID 1822316 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH2:9])[CH:5]=[C:4]([Br:10])[CH:3]=1>C1COCC1.[OH-].[OH-].[Pd+2]>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[C:4]([Br:10])[CH:3]=1

Participants

4

Reactant 1

HCID 186903433,5-Dibromostyrene

Product 1

HCID 187118073,5-DibromoethylbenzeneYield 74%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,3-dibromo-5-vinyl-benzene (4.55 g, 17.4 mmol) and 20% Pd(OH)2/C (2.0 g) in THF (60 mL) is purged with N2 and then H2, and the mixture is stirred under a H2 balloon at rt for 5 hours. The mixture is filtered through hyflo, and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 15/1 hexanes/ethyl acetate to afford 3.38 g (74%) of the title compound. Rf=0.63 (9/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3).

Workup

  1. customis purged with N2
  2. filtrationThe mixture is filtered through hyflo
  3. customthe solvent is removed in vacuo
  4. customto afford crude product that
  5. customis absorbed on silica gel
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-f6d75667a6c5418683af7cfd0c660276
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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