Chloride → HCID 54516793, compound

HRID 55296Notes

Reaction equation

HRID 55296 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1.[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15].[Cl-]>C(N(CC)CC)C.[Cu]I>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 312ChlorideHCID 66111TrimethylsilylacetyleneHCID 316783Methyl 2-(4-bromophenyl)acetate

Product 1

HCID 54516793HCID 54516793, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 20 g of 4-bromophenylacetic acid methyl ester and 10.3 g of trimethylsilylacetylene in 650 ml of triethylamine is refluxed in the presence of 1.46 g of bis-triphenylphosphinepalladium(II) chloride and 227 mg of copper(I) iodide for 5 hours. The reaction mixture is concentrated by evaporation, the residue is spread between water and ethyl acetate, the organic phase is washed with saturated common salt solution, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with hexane/0-5% ethyl acetate. 17.1 g of 4-(2-trimethylsilylethinyl)-phenylacetic acid methyl ester is obtained as oily crude product.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. washthe organic phase is washed with saturated common salt solution
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel with hexane/0-5% ethyl acetate

Sources & evidence

ORD record
ord-1dfc0b0dda894b629602d5f73bc01a98
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

Loading…