Dimethylformamide → (4-Bromophenylethynyl)trimethylsilane

HRID 486312

Reaction equation

HRID 486312 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.CN(C)C=O.C(N(CC)CC)C.[CH3:21][Si:22]([C:25]#[CH:26])([CH3:24])[CH3:23]>[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd](Cl)Cl.O>[CH3:21][Si:22]([C:25]#[C:26][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)([CH3:24])[CH3:23]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 114151-Bromo-2-iodobenzeneHCID 66111Trimethylsilylacetylene

Product 1

HCID 4226980(4-Bromophenylethynyl)trimethylsilaneYield 105.9%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 13169693Triphenylphosphine palladium dichlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 150 g of 97% bromo iodo benzene, 500 ml of anhydrous dimethylformamide, 100 ml of triethylamine, 50 g of trimethylsilyl acetylene, 2.1 g of copper iodide and 2.22 g of bis-(triphenylphosphine-palladium (II) dichloride was stirred for 2 hours and then 500 ml of ice-cooled water were added. The mixture was extracted 3 times with 500 ml of ethyl acetate and the organic phase was washed with salt water, then dried over sodium sulfate, and evaporated under reduced pressure to obtain 136.542 g of a brown oil which was purified by distillation under reduced pressure to obtain 106.979 g of the expected product with a boiling point of 75°-82° C. under 0.2 mbar and a melting point of 62° C.

Workup

  1. additionwere added
  2. extractionThe mixture was extracted 3 times with 500 ml of ethyl acetate
  3. washthe organic phase was washed with salt water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-03e6a71e8cec49c0b455f5e5760b9254
Source dataset
uspto-grants-1994_03
Patent number
US05290771

Linked notes

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