Triphenylamine → 4-Bromotriphenylamine

HRID 1417882Notes

Reaction equation

HRID 1417882 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]1([N:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C)C=O>[CH:25]1[CH:24]=[CH:23][C:22]([N:15]([C:9]2[CH:10]=[CH:11][C:12]([Br:1])=[CH:13][CH:14]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 11775TriphenylamineHCID 67184N-bromobutanimide

Product 1

HCID 6428384-BromotriphenylamineYield 61.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a 200 ml three-necked flask, 8.0 g (45 mmol) of N-bromosuccinimide and 10.0 g (41 mmol) of triphenylamine were placed, followed by 150 ml of N,N-dimethylformamide. The mixture was stirred overnight at room temperature. Next, N,N-dimethylformamide was removed from the reaction, and the resulting solid matter was extracted with carbon tetrachloride. Then, carbon tetrachloride was removed, and the reaction product was recrystallized twice from ethanol to give a white solid, 4-bromotriphenylamine in an amount of 8.2 g (yield: 61.7%).

Workup

  1. customNext, N,N-dimethylformamide was removed from the reaction
  2. extractionthe resulting solid matter was extracted with carbon tetrachloride
  3. customThen, carbon tetrachloride was removed
  4. customthe reaction product was recrystallized twice from ethanol

Sources & evidence

ORD record
ord-4c8ab958ff934c4a9665d639b96e738c
Source dataset
uspto-grants-1999_03
Patent number
US05879847

Reaction notes

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