Dimethylformamide → 4-Bromotriphenylamine

HRID 2296595Notes

Reaction equation

HRID 2296595 reaction equation
CN(C)C=O.[C:6]1([N:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Br:25]N1C(=O)CCC1=O>O>[Br:25][C:22]1[CH:21]=[CH:20][C:19]([N:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 11775TriphenylamineHCID 67184N-bromobutanimide

Product 1

HCID 6428384-BromotriphenylamineYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 500 ml of dry dimethylformamide, 50 g (200 mmole) of triphenylamine was dissolved. To the obtained solution, a solution prepared by dissolving 36 g (200 mmole) of N-bromosuccinimide into 100 ml of dry dimethylformamide was added and the obtained solution was stirred at the room temperature for 6 hours. After the reaction was completed, 1 liter of water was added to the reaction mixture and the formed precipitates were separated by filtration. The obtained light yellow solid was washed with water, dried at a reduced pressure and recrystallized from hexane and 38 g (the yield: 59%) of white needle crystals of the subject compound was obtained.

Workup

  1. customTo the obtained solution, a solution prepared
  2. additionwas added
  3. customthe formed precipitates
  4. customwere separated by filtration
  5. washThe obtained light yellow solid was washed with water
  6. customdried at a reduced pressure
  7. customrecrystallized from hexane and 38 g (the yield: 59%) of white needle crystals of the subject compound
  8. customwas obtained

Sources & evidence

ORD record
ord-e496b41ec5254e9786b9241f7dea6cd1
Source dataset
uspto-grants-2002_12
Patent number
US06489046B1

Reaction notes

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