Trimethylsilylacetylene → ((4-Chloro-2-fluorophenyl)ethynyl)trimethylsilane

HRID 508825

반응식

HRID 508825 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([F:9])[CH:3]=1.[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])#[CH:11]>CS(C)=O.[Cu](I)I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]#[C:10][Si:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([F:9])[CH:3]=1

참가 물질

6

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 27365624-Chloro-2-fluoro-1-iodobenzene

생성물 1

HCID 90019293((4-Chloro-2-fluorophenyl)ethynyl)trimethylsilane수율 56.5%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of 4-chloro-2-fluoro-1-iodobenzene (2.0 g, 7.8 mmol) in DMSO (10 mL) was added ethynyl(trimethyl)silane (1.14 g, 11.0 mmol), copper iodide (0.029 g, 0.15 mmol), bis(triphenylphosphine) palladium(II) chloride (0.218 g, 0.3 mmol) and TEA (1 mL). The reaction mass was stirred at RT for 4-5 h. The reaction mass quenched in water, passed through celite bed and extracted with ethyl acetate and concentrated to afford 1.0 g of desired product.

후처리

  1. customThe reaction mass quenched in water
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-138134a5f9054324b8f30cc060a031ea
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096545B2

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