1-Ethynyl-4-methoxybenzene → 1-[4-(4-Methoxyphenylethynyl)phenoxy]-2-diethylaminoethane

HRID 1648721Notes

Reaction equation

HRID 1648721 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[CH:25])=[CH:20][CH:19]=1>C(N(CC)CC)C.[Pd].[Cu]I>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[C:25][C:2]2[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 2510201-Ethynyl-4-methoxybenzeneHCID 4239532-(4-bromophenoxy)-N,N-diethylethanamine

Product 1

HCID 204815621-[4-(4-Methoxyphenylethynyl)phenoxy]-2-diethylaminoethaneYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 15 g (0.06 mole) of 1-(4-bromophenoxy)-2-diethylaminoethane and 8.2 g (0.062 mole) of 4-methoxyphenylacetylene in 150 ml of triethylamine are added, under nitrogen, 420 mg of the palladium complex PdCl2 [P(C6H5)2 ]2 and 228 mg of copper(I) iodide. The reaction mixture is subsequently refluxed for 24 hours, then concentrated, and the residue is taken up in water. After extraction with 200 ml of ether, the combined ethereal phases are washed 3 times with water, dried and evaporated to dryness. The crude product is chromatographed on silica gel, affording 15.5 g (80%) of 1-[4-(4-methoxyphenylethynyl)phenoxy]-2-diethylaminoethane with a melting point of 59°-60° C.

Workup

  1. temperatureThe reaction mixture is subsequently refluxed for 24 hours
  2. concentrationconcentrated
  3. extractionAfter extraction with 200 ml of ether
  4. washthe combined ethereal phases are washed 3 times with water
  5. customdried
  6. customevaporated to dryness
  7. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-2a39689c8236429aa40f690711c5e80e
Source dataset
uspto-grants-1983_11
Patent number
US04412856

Reaction notes

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