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

HRID 59334

반응식

HRID 59334 반응식
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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 8857Ethyl Acetate용매

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온도
55 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-db091dd852e94dac8377a99e56e3cd33
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09439890B2

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