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

HRID 1988369ノート

反応式

HRID 1988369 の反応式
[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]

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 83717Copper iodide触媒HCID 178418903HCID 178418903、化合物触媒HCID 8471Triethylamine溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-264d5db6b1a74ad7b9bdffb802943d4d
出典データセット
uspto-grants-2009_06
特許番号
US07553972B2

反応ノート

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