1-Bromo-2-iodobenzene → 1-Bromo-2-(3-methyl-butyl)-benzene

HRID 1436518Notes

Reaction equation

HRID 1436518 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Br:8].[CH3:9][CH:10]([CH3:14])[CH2:11][CH2:12][Zn]>C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd]>[Br:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH2:12][CH2:11][CH:10]([CH3:14])[CH3:9]

Participants

4

Reactant 2

HCID 114151-Bromo-2-iodobenzeneHCID 178445878HCID 178445878, compound

Product 1

HCID 210637691-Bromo-2-(3-methyl-butyl)-benzeneYield 78.1%

Reagents, catalysts & solvents 1

HCID 72499888Dibenzalacetone palladiumCatalyst

Procedure

Charge a Schlenck flask with palladium dibenzylidene acetone (88 mg, 0.16 mmol) and tri-o-furyl phosphine (72 mg, 0.31 mmol), purge with nitrogen and add 2 ml of dry THF. Stir for 2 minutes, until the deep purple solution turns to greenish yellow and add 1-iodo-2-bromo benzene (0.8 ml. 6.2 mmol) followed by 3-methyl-butyl zinc (0.5 M solution in THF, 30 ml, 15 mmol). React at rt for 4 hours. Add silica gel, concentrate, load onto a flash chromatography column and elute with hexane to obtain the title compound as a colorless liquid (1.1 g, 75%).

Workup

  1. custompurge with nitrogen
  2. additionadd 2 ml of dry THF
  3. customReact at rt for 4 hours
  4. concentrationAdd silica gel, concentrate
  5. washload onto a flash chromatography column and elute with hexane

Sources & evidence

ORD record
ord-403cd73f02314f6fbadf2e87ea6ae88d
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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