Phenylacetylene → 4-(Phenylethynyl)benzil

HRID 1595948Notes

Reaction equation

HRID 1595948 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[O:9])=[CH:4][CH:3]=1.[C:18]1([C:24]#[CH:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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>[C:18]1([C:24]#[C:25][C:2]2[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:11])=[O:9])=[CH:4][CH:3]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 2367011-(4-Bromophenyl)-2-phenylethane-1,2-dione

Product 1

HCID 110881914-(Phenylethynyl)benzil

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

4-Bromobenzil (10.0 g, 0.0346 mol), phenylacetylene (3.88 g, 0.0380 mol), and (PPh3)2PdCl2 (0.121 g, 0.0002 mol) in diethylamine (950 mL) is stirred at ambient temperature for 72 hours, followed by concentration to dryness. The residue is then taken up in methylene chloride. Standard aqueous workup followed by recrystallization from 2-propanol gives the title compound.

Workup

  1. concentrationfollowed by concentration to dryness
  2. customStandard aqueous workup followed by recrystallization from 2-propanol

Sources & evidence

ORD record
ord-071f6f28603845aead5c2722c666b91c
Source dataset
uspto-grants-2001_09
Patent number
US06288188B1

Reaction notes

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