Sodium Carbonate → 2-Phenylanthracene

HRID 889786Notes

Reaction equation

HRID 889786 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:24]=[CH:23][C:22]2[C:13](=[CH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[C:1]1([C:18]2[CH:17]=[CH:16][C:15]3[C:20](=[CH:21][C:22]4[C:13]([CH:14]=3)=[CH:12][CH:11]=[CH:24][CH:23]=4)[CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 123460992-Bromoanthracene

Product 1

HCID 5197172-PhenylanthraceneYield 75.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, 14.5 g of phenylboronic acid, 25.7 g of 2-bromoanthracene, 4.62 g of tetraxis(triphenylphosphine)palladium(0), 400 mL of toluene and 200 mL of a 2M aqueous solution of sodium carbonate were mixed. The resultant was refluxed with stirring for 8 hours. After cooling to room temperature, deposited crystals were separated by filtration. By repetition of recrystallization and washing of the obtained solids using toluene-hexane, 19.1 g (yield: 75%) of 2-phenylanthracene was obtained.

Workup

  1. temperatureThe resultant was refluxed
  2. customwere separated by filtration
  3. customBy repetition of recrystallization
  4. washwashing of the obtained solids

Sources & evidence

ORD record
ord-d83ece5686b7470693b2f7dce7a189e4
Source dataset
uspto-grants-2012_08
Patent number
US08253129B2

Reaction notes

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