Trimethylsilylacetylene → Methyl 2-chloro-5-((trimethylsilyl)ethynyl)benzoate

HRID 1988369노트

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HRID 1988369 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](I)[CH:7]=[CH:6][C:5]=1[Cl:11].[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15]>C(N(CC)CC)C.Cl[Pd-2](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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[CH:7]=[CH:6][C:5]=1[Cl:11]

참가 물질

7

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 35563912Methyl 2-chloro-5-iodobenzoate

생성물 1

HCID 57422929Methyl 2-chloro-5-((trimethylsilyl)ethynyl)benzoate수율 98.1%

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 83717Copper iodide촉매HCID 178418903HCID 178418903, 화합물촉매HCID 8471Triethylamine용매

실험 절차

A mixture of 2-chloro-5-iodo-benzoic acid methyl ester (3.5 g, 12 mmol), dichlorobis(triphenylphosphino)palladium (II) (0.04 g, 0.06 mmol), triphenylphosphine (0.06 g, 0.24 mmol), copper iodide (0.05 g, 0.24 mmol), (trimethylsilyl)acetylene (1.9 g, 19.2 mmol) in triethylamine (40 mL) was heated at reflux for 12 h. The mixture was concentrated in vacuo, diluted with ethyl acetate (150 mL) and washed sequentially with 10% aqueous citric acid, water, and brine. The organic solution was dried, filtered and concentrated in vacuo to afford the title compound (3.14 g).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. concentrationThe mixture was concentrated in vacuo
  4. additiondiluted with ethyl acetate (150 mL)
  5. washwashed sequentially with 10% aqueous citric acid, water, and brine
  6. customThe organic solution was dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-264d5db6b1a74ad7b9bdffb802943d4d
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553972B2

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