Water → 4-Bromotriphenylamine

HRID 2122066Notes

Reaction equation

HRID 2122066 reaction equation
[C:1]1([N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:20][C:17]1[CH:16]=[CH:15][C:14]([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11775TriphenylamineHCID 67184N-bromobutanimide

Product 1

HCID 6428384-BromotriphenylamineYield 30.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

In a 2000 ml two neck round bottom flask, 250 g of triphenylamine and 1000 ml of N,N′-dimethylformamide were charged, and the mixture was dissolved by heating to 40° C. A solution (450 ml) prepared by dissolving 190 g of N-bromosuccinimide in N,N′-dimethylformamide was slowly added dropwise using a dropping funnel at room temperature with vigorously stirring and, after the completion of the dropwise addition, the reaction was continuously performed for 1 hour. After the completion of the reaction, 1 ml of water was introduced in the reaction solution and the solvent was removed under reduced pressure. Then, 500 ml of water was added to deposit a product. The deposit was filtered, dried under reduced pressure and then purified by distillation under reduced pressure to obtain 100 g of N-(4-bromophenyl)-N-phenyl-aminobenzene.

Workup

  1. dissolutionthe mixture was dissolved
  2. additionwas slowly added dropwise
  3. customat room temperature
  4. additionafter the completion of the dropwise addition
  5. additionwas introduced in the reaction solution
  6. customthe solvent was removed under reduced pressure
  7. additionThen, 500 ml of water was added
  8. filtrationThe deposit was filtered
  9. customdried under reduced pressure
  10. distillationpurified by distillation under reduced pressure

Sources & evidence

ORD record
ord-de93093a6c304e2387354a9b7c21920d
Source dataset
uspto-grants-2004_02
Patent number
US06696588B2

Reaction notes

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