Trimethylsilylacetylene → 1-[(Trimethylsilyl)ethynyl]-3-(trifluoromethyl)benzene

HRID 508827ノート

反応式

HRID 508827 の反応式
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1.[C:12]([Si:14]([CH3:17])([CH3:16])[CH3:15])#[CH:13]>C(OCC)(=O)C.[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>[CH3:15][Si:14]([CH3:17])([CH3:16])[C:12]#[C:13][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1

参加物

6

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 67868Benzene, 1-iodo-3-(trifluoromethyl)-

生成物 1

HCID 42818851-[(Trimethylsilyl)ethynyl]-3-(trifluoromethyl)benzene収率 57.3%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
55 °C

実験手順

To a solution of 1-iodo-3-(trifluoromethyl)benzene (1.0 g, 3.6 mmol) in ethyl acetate (20 mL) was added ethynyl(trimethyl)silane (0.540 g, 5.5 mmol), copper iodide (0.042 g, 0.22 mmol), bis(triphenylphosphine) palladium(II) chloride (0.129 g, 0.18 mmol) and TEA (2.2 mL, 14.7 mmol). The reaction mass stirred at 50-60° C. for 24 h. The reaction mass was quenched in water, extracted with ethyl acetate and concentrated to afford 0.500 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 0.26 (s, 9H), 7.44 (t, J=7.8 Hz, 1H), 7.55 (d, J=7.8 Hz, 1H), 7.62 (d, J=7.2 Hz, 1H), 7.72 (s, 1H).

後処理

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

出典と根拠

ORDレコード
ord-f2fa04a6e9be4f1489aada74d91affb4
出典データセット
uspto-grants-2015_08
特許番号
US09096545B2

反応ノート

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