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

HRID 271108노트

반응식

HRID 271108 반응식
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

참가 물질

5

반응물 2

HCID 164493-BromobiphenylHCID 66111Trimethylsilylacetylene

생성물 1

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

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매

실험 절차

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+.

후처리

  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)

출처 및 근거

ORD 기록
ord-65c875ef60d8490dbfbe4e5a2ace50f6
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452885B2

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