Phenylacetylene → HCID 3522678, compound

HRID 1595954Notes

Reaction equation

HRID 1595954 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)=[O:11])=[O:9])=[CH:4][CH:3]=1.[C:19]1([C:25]#[CH:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(NCC)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>[C:19]1([C:25]#[C:26][C:2]2[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]3[CH:17]=[CH:16][C:15]([C:10]#[C:8][C:5]4[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=4)=[CH:14][CH:13]=3)=[O:11])=[O:9])=[CH:4][CH:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 2

HCID 10821PhenylacetyleneHCID 964304,4'-Dibromobenzil

Product 1

HCID 3522678HCID 3522678, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

A solution of 4,4′-dibromobenzil (15.8 g, 0.0431 mol), phenylacetylene (5.06 g, 0.0495 mol), (PPh3)2PdCl2 (0.151 g, 0.0002 mol) and CuI (0.820 g, 0.0043 mol) in diethylamine (150 mL) is heated at reflux overnight. The reaction mixture is concentrated to dryness, then taken up in CH2Cl2 (150 mL), washed with 1 M HCl, 10 percent Na2CO3/H2O, brine and dried (Na2SO4), then concentrated. Crystallization from 2-propanol gives 7.92 g (45 percent) as a light tan solid, mp 168° C. to 170° C. 1H NMR (CDCl3) δ 7.97 (d, J=8.2 Hz, 4H), 7.64 (d, J=8.2 Hz, 4H), 7.55 (m, 4H), 7.37 (m, 6H); 13C NMR (CDCl3) δ 193.03, 132.46, 132.03, 131.82, 130.21, 129.84, 129.06, 128.47, 122.37, 94.28, 88.55.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture is concentrated to dryness
  3. washwashed with 1 M HCl, 10 percent Na2CO3/H2O, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customCrystallization from 2-propanol
  7. customgives 7.92 g (45 percent) as a light tan solid, mp 168° C. to 170° C

Sources & evidence

ORD record
ord-b48f83e9497744ee91c4e7fc7f8d6815
Source dataset
uspto-grants-2001_09
Patent number
US06288188B1

Reaction notes

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