2-Chloroanthracene → 2-Phenylanthracene

HRID 221178Notes

Reaction equation

HRID 221178 reaction equation
Cl[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C1(C)C=CC=CC=1>[C:16]1([C:2]2[CH:15]=[CH:14][C:13]3[C:4](=[CH:5][C:6]4[C:11]([CH:12]=3)=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH:3]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 283082-ChloroanthraceneHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic Acid

Product 1

HCID 5197172-PhenylanthraceneYield 83.6%

Reagents, catalysts & solvents 2

HCID 75806TricyclohexylphosphineCatalystHCID 1140TolueneSolvent2×

Procedure

Into a flask, 5.00 g of 2-chloroanthracene, 4.3 g of phenylboronic acid, 538 mg of tris(dibenzylieneacetone)dipalladium(0), 494 mg of tricyclohexyl phosphine, 9.98 g of tripotassium phosphate, and 75 ml of toluene were put, and the solution was stirred at reflux temperature for 2 hours under argon atmosphere. After heating, 1.5 liter of toluene was added to the reaction liquid, the liquid was cooled to room temperature and then filtrated, and thus the filtrates were purified by silica gel column chromatography. The filtrates were concentrated in an evaporator, the concentrates were recrystallized in toluene, and thus 5.0 g of 2-phenylanthracene was obtained.

Workup

  1. temperatureat reflux temperature for 2 hours under argon atmosphere
  2. temperatureAfter heating
  3. filtrationfiltrated
  4. customthus the filtrates were purified by silica gel column chromatography
  5. concentrationThe filtrates were concentrated in an evaporator
  6. customthe concentrates were recrystallized in toluene

Sources & evidence

ORD record
ord-7e977a05d39941088a05831005e7e0cd
Source dataset
uspto-grants-2012_06
Patent number
US08202633B2

Reaction notes

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