1,4-Dibromobenzene → 2-(4-Bromophenyl)-9,10-diphenylanthracene

HRID 571592Notes

Reaction equation

HRID 571592 reaction equation
[C:1]1([C:7]2[C:8]3[C:13]([C:14]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[C:15]4[C:20]=2[CH:19]=[C:18](B(O)O)[CH:17]=[CH:16]4)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:31]1[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[Br:37][C:34]1[CH:35]=[CH:36][C:31]([C:11]2[CH:10]=[CH:9][C:8]3[C:13](=[C:14]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:15]4[C:20]([C:7]=3[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:12]=2)=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 78041,4-DibromobenzeneHCID 10340Sodium CarbonateHCID 231602159,10-Diphenylanthracene-2-boronic Acid

Product 1

HCID 575364702-(4-Bromophenyl)-9,10-diphenylanthraceneYield 51.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

An amount of 3.74 g (10 mmol) of 9,10-diphenylanthracene-2-boronic acid synthesized in the same manner as in Exemplary Synthesis 1, 9.44 g (40 mmol) of p-dibromobenzene, and 300 mg of tetrakis triphenylphosphine palladium as catalysis were dissolved in a mixed solvent of 60 ml of toluene and 15 ml of ethanol. Then, 30 ml of 2M sodium carbonate solution was added 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 2.32 g (5.15 mmol) of 2-(4-bromophenyl)-9,10-diphenylanthracene. The yield was 51.5%.

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-e74358eee9344eb88bfca9217bf5c3b0
Source dataset
uspto-grants-2015_05
Patent number
US09028976B2

Reaction notes

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