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

HRID 271108ノート

反応式

HRID 271108 の反応式
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

参加物

5

反応物 2

HCID 164493-BromobiphenylHCID 66111Trimethylsilylacetylene

生成物 1

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

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒

実験手順

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+.

後処理

  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)

出典と根拠

ORDレコード
ord-65c875ef60d8490dbfbe4e5a2ace50f6
出典データセット
uspto-grants-2008_11
特許番号
US07452885B2

反応ノート

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