Phenylacetylene → HCID 67158074, compound

HRID 548552Notes

Reaction equation

HRID 548552 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][O:10][C:11](=[O:32])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[C:23][C:24]2[CH:29]=[C:28](Br)[CH:27]=[C:26](Br)[CH:25]=2)=[CH:16][CH:15]=1>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:9][O:10][C:11](=[O:32])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[C:23][C:24]2[CH:29]=[C:28]([C:8]#[C:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:27]=[C:26]([C:8]#[C:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:25]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 10821PhenylacetyleneHCID 67157543HCID 67157543, compound

Product 1

HCID 67158074HCID 67158074, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of phenylacetylene (0.20 g, 1.98 mmol), {4-[3-(3,5-dibromo-phenyl)-prop-2-ynyloxy]-phenoxy}-acetic acid methyl ester (0.3 g, 0.66 mmol), Pd(PPh3)4 (0.11 g, 0.1 mmol) and CuI (0.05 g, 0.26 mmol) in triethylamine (10 ml) was heated in a sealed tube in a microwave own at 65° C. for 1 hour. The reaction mixture was filtered and the filtrate was evaporated. The residue was purified on HPLC using acetonitril/water as eluent to give {4-[3-(3,5-bis-phenylethynyl-phenyl)-prop-2-ynyloxy]-phenoxy}-acetic acid methyl ester in 150 mg (46%) yield.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was purified on HPLC

Sources & evidence

ORD record
ord-623cb3b5ae1342879cf1bdacad994989
Source dataset
uspto-grants-2011_05
Patent number
US07943612B2

Reaction notes

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