Triethylamine → 2-[2-(2-Methoxyphenyl)-ethynyl]-5-methoxybenzaldehyde

HRID 1006913Notes

Reaction equation

HRID 1006913 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10])#[CH:2].Br[C:12]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:13]=1[CH:14]=[O:15].C(N(CC)CC)C>CN(C)C=O>[CH3:10][O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]#[C:2][C:12]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:13]=1[CH:14]=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3444802-Bromo-5-methoxybenzaldehydeHCID 5829121-Ethynyl-2-methoxybenzene

Product 1

HCID 225030652-[2-(2-Methoxyphenyl)-ethynyl]-5-methoxybenzaldehydeYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The resulting 2-ethynylanisole (0.79 g) and 2-bromo-5-methoxybenzaldehyde (1.14 g) were reacted in dimethylformamide (50 ml) in the presence of dichloro-bis-triphenylphosphine palladium (1.0 g), cuprous iodide (0.5 g) and triethylamine (15 ml), in nitrogen atmosphere at 50° C. for 6 hr. The resulting reaction solution was evaporated, and to the resulting residue were added ethyl acetate and water. The resulting organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give 0.95 g of the title compound as a pale yellow oil.

Workup

  1. customThe resulting reaction solution
  2. customwas evaporated
  3. additionto the resulting residue were added ethyl acetate and water
  4. washThe resulting organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-94b54cc142344360b4c618b0f698db78
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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