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

HRID 271124

Reaction equation

HRID 271124 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 is 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 and filtered. The filtrate was concentrated and the concentrate 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 filtrate was concentrated
  5. customthe concentrate was purified by chromatography (silica gel, EtOAc/hexane: 5/95)

Sources & evidence

ORD record
ord-748716f3ddd1422b9b7596085480e3cf
Source dataset
uspto-grants-2008_11
Patent number
US07452885B2

Linked notes

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