2-Bromobenzaldehyde → HCID 15181386, compound

HRID 1590219Notes

Reaction equation

HRID 1590219 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]#[CH:12].Br[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=[O:17]>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]#[C:12][C:21]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17]

Participants

6

Reactant 2

HCID 811292-BromobenzaldehydeHCID 1150172-Ethynylnaphthalene

Product 1

HCID 15181386HCID 15181386, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 15.3 g of naphth-2-yl-acetylene and 16.65 g of -bromobenzaldehyde in 120 ml of absolute triethylamine were added at a bath temperature of 50° C. while stirring in an atmosphere of dry nitrogen 1.05 g of bis-(triphenylphosphine)-palladium(II) chloride and 0.07 g of copper(I) iodide. Then the mixture was stirred at a bath temperature of 70°-80° C. (TLC: petroleum ether/ether-5:1). When the reaction was finished the mixture was filtered, the residue washed with ethyl acetate and then the filtrates were evaporated in a vacuum. By column chromatography with petroleum ether/ether (4:1) the residue is purified to yield 15.1 g (65.5% of the theoretical yield) of the title compound in the form of crystals melting at 90°-92° C.

Workup

  1. filtrationwas filtered
  2. washthe residue washed with ethyl acetate
  3. customthe filtrates were evaporated in a vacuum
  4. customBy column chromatography with petroleum ether/ether (4:1) the residue is purified
  5. customto yield 15.1 g (65.5% of the

Sources & evidence

ORD record
ord-0d6174e09e50496488e9dc0169bdf186
Source dataset
uspto-grants-1993_04
Patent number
US05202349

Reaction notes

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