3-Bromobiphenyl → [([1,1'-Biphenyl]-3-yl)ethynyl](trimethyl)silane

HRID 271108Notes

Reaction equation

HRID 271108 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:14]([Si:16]([CH3:19])([CH3:18])[CH3:17])#[CH:15]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[C:4]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=[C:2]([C:15]#[C:14][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:3]=1

Participants

5

Reactant 2

HCID 164493-BromobiphenylHCID 66111Trimethylsilylacetylene

Product 1

HCID 59834575[([1,1'-Biphenyl]-3-yl)ethynyl](trimethyl)silaneYield 88.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

To a solution of 3-bromo-1,1′-biphenyl (5.06 g, 21.76 mmol) in TEA (20 mL) are added dichlorobis(triphenylphosphine)palladium (0.47 g, 0.65 mmol), copper iodide (0.08 g, 0.44 mmol) and ethynyl(trimethyl)silane (4.62 mL, 32.64 mmol). The reaction mixture is refluxed for 3 h and cooled to room temperature. After evaporation of the solvent, the crude material is purified by chromatography (silica gel, 100% hexane) to afford the title compound (4.81 g, 88%) as an oil. MS (+) EI: 250 M+.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 h
  2. customAfter evaporation of the solvent
  3. customthe crude material is purified by chromatography (silica gel, 100% hexane)

Sources & evidence

ORD record
ord-65c875ef60d8490dbfbe4e5a2ace50f6
Source dataset
uspto-grants-2008_11
Patent number
US07452885B2

Reaction notes

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