Triphenylamine → 4-Bromotriphenylamine

HRID 843306Notes

Reaction equation

HRID 843306 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%

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: 61.0%).

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-af025dd975264ee890f7b99bc99a9a0a
Source dataset
uspto-grants-2002_04
Patent number
US06376695B1

Reaction notes

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