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

HRID 508827Notes

Reaction equation

HRID 508827 reaction equation
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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-f2fa04a6e9be4f1489aada74d91affb4
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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