Sodium Carbonate → 9-Phenylanthracene

HRID 571587Notes

Reaction equation

HRID 571587 reaction equation
Br[C:2]1[C:3]2[C:8]([CH:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[C:16]1([C:2]2[C:3]3[C:8]([CH:9]=[C:10]4[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]4)=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 740629-Bromoanthracene

Product 1

HCID 117669-PhenylanthraceneYield 91.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

An amount of 15.14 g (58.9 mmol) of 9-bromoanthracene, 7.2 g (59 mmol) of phenylboronic acid, and 1 g of tetrakis triphenylphosphine palladium as catalysis were dissolved in a mixed solvent of 100 ml of toluene and 25 ml of ethanol. Then, 50 ml of 2M sodium carbonate solution was added to the mixed solvent and allowed to react at 90° C. for 12 hours. After the reaction was completed, the organic layer was separated and purified by column chromatography to obtain 13.65 g (53.7 mmol) of 9-phenylanthracene. The yield was 91.2%.

Workup

  1. customto react at 90° C. for 12 hours
  2. customthe organic layer was separated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-4f822aa04d5e43dc89a5daa226b55c6b
Source dataset
uspto-grants-2015_05
Patent number
US09028976B2

Reaction notes

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