Phenylacetylene → HCID 70974553, compound

HRID 1424562Notes

Reaction equation

HRID 1424562 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4](Br)[CH:3]=1.[C:12]1([C:18]#[CH:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCN(CC)CC.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>[N+:8]([C:6]1[CH:7]=[C:2]([C:19]#[C:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=[C:4]([C:19]#[C:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=1)([O-:10])=[O:9]

Participants

6

Reactant 2

HCID 10821PhenylacetyleneHCID 2387111,3-dibromo-5-nitrobenzene

Product 1

HCID 70974553HCID 70974553, compoundYield 51%

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 1,3-dibromo-5-nitrobenzene (0.56 g, 2.00 mmol), bis(triphenylphosphine)palladium(II) chloride (0.10 g, 0.14 mmol) and copper(I) iodide (0.027 g, 0.14 mmol) in Et3N was degassed (three times). Phenylacetylene (0.50 g, 4.88 mmol) was added and mixture was stirred overnight. The reaction mixture was filtered through a celite pad and the pad was rinsed with CH2Cl2. The filtrate was washed with brine and the organic layer was dried with (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (Dichloromethane;Hexane=1:10) to afford ((5-nitro-1,3-phenylene)bis(ethyne-2,1-diyl))dibenzene (0.33 g, 51% yield): 1H-NMR (400 MHz, CDCl3) δ 8.30 (d, J=1.3 Hz, 2H), 7.96 (t, J=1.3 Hz, 1H), 7.56 (m, 4H), 7.40 (m, 6H).

Workup

  1. customwas degassed (three times)
  2. filtrationThe reaction mixture was filtered through a celite pad
  3. washthe pad was rinsed with CH2Cl2
  4. washThe filtrate was washed with brine
  5. dry with materialthe organic layer was dried with (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (Dichloromethane;Hexane=1:10)

Sources & evidence

ORD record
ord-618a79a0d1b84702a6ae345248025b79
Source dataset
uspto-grants-2015_01
Patent number
US08927728B2

Reaction notes

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