Trimethylsilylacetylene → {[4-(Difluoromethoxy)phenyl]ethynyl}(trimethyl)silane

HRID 2220451Notes

Reaction equation

HRID 2220451 reaction equation
[F:1][CH:2]([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1.[C:12]([Si:14]([CH3:17])([CH3:16])[CH3:15])#[CH:13]>C(N(CC)CC)C.C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu](I)I>[F:1][CH:2]([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:13]#[C:12][Si:14]([CH3:17])([CH3:16])[CH3:15])=[CH:6][CH:5]=1

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 27370081-(Difluoromethoxy)-4-iodobenzene

Product 1

HCID 68699091{[4-(Difluoromethoxy)phenyl]ethynyl}(trimethyl)silaneYield 96%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 1-(difluoromethoxy)-4-iodobenzene (12.7 g, 50 mmol) in triethylamine (175 mL) was treated with tetrakis(triphenylphosphine)palladium (4.0 g, 3.5 mmol), copper iodide (925 mg, 4.85 mmol), and a solution of ethynyl(trimethyl)silane (6.9 mL, 50 mmol) in acetonitrile at room temperature, stirred for 1 h at 60° C. and concentrated in vacuo. The resultant residue was dissolved in Et2O, filtered and the filtrated was concentrated in vacuo. This residue was purified by chromatography (silica gel, EtOAc/hexane: 5/95) to give {[4-(difluoromethoxy)-phenyl]ethynyl}(trimethyl)silane (11.5 g, 96%) as an oil.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resultant residue was dissolved in Et2O
  3. filtrationfiltered
  4. concentrationthe filtrated was concentrated in vacuo
  5. customThis residue was purified by chromatography (silica gel, EtOAc/hexane: 5/95)

Sources & evidence

ORD record
ord-6bf8a1d705974e239ec69760e0b7f8b2
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

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