Triphenylamine → 4-Bromotriphenylamine

HRID 357470Notes

Reaction equation

HRID 357470 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-Bromotriphenylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.0 g (45 mmol) of N-bromosuccinimide and 10.0 g (41 mmol) of triphenylamine were placed in a 200 mL three-neck flask and then 150 mL of N,N-dimethylformamide was added. The mixture were stirred overnight at room temperature. N,N-dimethylformamide was removed, and the obtained solid was extracted with carbon tetrachloride. The solvent was removed, and the crude product was twice recrystallized from ethanol. As a result, a white solid of 4-bromotriphenylamine was obtained in an amount of 8.2 g (61.7%).

Workup

  1. customN,N-dimethylformamide was removed
  2. extractionthe obtained solid was extracted with carbon tetrachloride
  3. customThe solvent was removed
  4. customthe crude product was twice recrystallized from ethanol

Sources & evidence

ORD record
ord-e448720861b34dca82e7572223bf7976
Source dataset
uspto-grants-1998_11
Patent number
US05840816

Reaction notes

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