Trimethylsilylacetylene → [2-(3,5-Dichlorophenyl)ethynyl]trimethylsilane

HRID 413938노트

반응식

HRID 413938 반응식
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([Cl:9])[CH:3]=1.[CH3:10][Si:11]([C:14]#[CH:15])([CH3:13])[CH3:12]>C(NCC)C.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>[Cl:1][C:2]1[CH:7]=[C:6]([C:15]#[C:14][Si:11]([CH3:13])([CH3:12])[CH3:10])[CH:5]=[C:4]([Cl:9])[CH:3]=1

참가 물질

6

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 764241,3-Dichloro-5-iodobenzene

생성물 1

HCID 22570337[2-(3,5-Dichlorophenyl)ethynyl]trimethylsilane

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8021Diethylamine용매

실험 절차

To a solution of 1,3-dichloro-5-iodo-benzene (5.44 g, 20 mmol) in diethylamine (75 mL) was added PdCl2(PPh3)2 (280 mg, 0.4 mmol), trimethylsilylacetylene (2.36 g, 24.0 mmol) and copper(I)iodide (20 mg, 0.1 mmol). The reaction mixture was stirred at room temperature for 24 h, filtered and evaporated. The residue was purified by column chromatography using heptane:ethyl acetate (8:2) as eluent. The desired (3,5-dichloro-phenylethynyl)-trimethylsilane product was isolated in 4.85 g yield.

후처리

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-061369dd3e2d4ce58ce9ce7d9fca3fbb
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06569901B2

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