1,4-Dibromobenzene → 9-(4-Bromophenyl)-10-phenylanthracene

HRID 571590Notes

Reaction equation

HRID 571590 reaction equation
[C:1]1([C:7]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](B(O)O)=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[CH:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:24][C:25]1[CH:30]=[CH:29][C:28](Br)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[C:1]1([C:7]2[C:20]3[C:15]([C:14]([C:28]4[CH:29]=[CH:30][C:25]([Br:24])=[CH:26][CH:27]=4)=[C:13]4[C:8]=2[CH:9]=[CH:10][CH:11]=[CH:12]4)=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 78041,4-DibromobenzeneHCID 10340Sodium CarbonateHCID 22247164(10-Phenylanthracen-9-yl)boronic acid

Product 1

HCID 221382759-(4-Bromophenyl)-10-phenylanthraceneYield 43.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

An amount of 2.46 g (8.26 mmol) of 10-phenylanthracene-9-boronic acid synthesized in the same manner as in Exemplary Synthesis 2, 9.75 g (41.3 mmol) of p-dibromobenzene, and 250 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 1.48 g (3.62 mmol) of 9-phenyl-10-(4-bromophenyl)anthracene. The yield was 43.8%.

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-6ec1d3a6f8d44fc293982f09f53bbee1
Source dataset
uspto-grants-2015_05
Patent number
US09028976B2

Reaction notes

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