9-Phenylanthracene → 9-Bromo-10-phenyl-anthracene

HRID 411955

Reaction equation

HRID 411955 reaction equation
[C:1]1([C:7]2[C:8]3[C:13]([CH:14]=[C:15]4[C:20]=2[CH:19]=[CH:18][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:21]Br>ClCCl>[Br:21][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[CH:19]2

Participants

4

Reactant 2

HCID 117669-PhenylanthraceneHCID 24408Bromine

Product 1

HCID 41558369-Bromo-10-phenyl-anthraceneYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 9-phenylanthracene (10 grams) and ferric chloride (0.065 gram) in 100 milliliters of dichloromethane were added 6.70 grams of bromine in 30 milliliters of dichloromethane through an addition funnel at room temperature. The reaction mixture was stirred for 3 hours, and then washed with aqueous sodium thiosulfate and water. After removal of the solvents, the crude residue was recrystallized from ethanol to yield 12.5 grams of 10-bromo-9-phenylanthracene. The structure of this compound was confirmed by proton NMR analysis.

Workup

  1. washwashed with aqueous sodium thiosulfate and water
  2. customAfter removal of the solvents
  3. customthe crude residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-f28d0d0b7c674e91828aec858feb3a3f
Source dataset
uspto-grants-2003_05
Patent number
US06562485B2

Linked notes

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