N-bromobutanimide → N-(4-Bromophenyl)-4-biphenylamine

HRID 719038Notes

Reaction equation

HRID 719038 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[Br:20]N1C(=O)CCC1=O>CN(C=O)C>[C:1]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:2]=[CH:3][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([Br:20])=[CH:10][CH:9]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 13087229N-phenyl-(1,1'-biphenyl)-4-amine

Product 1

HCID 57746339N-(4-Bromophenyl)-4-biphenylamineYield 284.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(Biphenyl-4-yl)-phenylamine (35.0 g) and DMF (700 ml) were added and dissolved in a nitrogen-substituted reaction vessel, and N-bromosuccinimide (8.5 g) was added under ice-cooled conditions. The reaction temperature was raised to room temperature while adding N-bromosuccinimide (17.0 g) in two separate portions. After being stirred for 25.5 hours, the reaction solution was dropped to water (3,500 ml), and the precipitated solid was collected by filtration. Toluene (2,500 ml) was added to dissolve the solid, and the solid was dried over magnesium sulfate. After filtration, the filtrate was concentrated. The resulting concentrate was dispersed and washed by addition of n-hexane (500 ml), and dried overnight under reduced pressure to obtain a reddish solid of (biphenyl-4-yl)-(4-bromophenyl)amine (44.1 g; yield 95.4%).

Workup

  1. additionwas added under ice-
  2. temperaturecooled conditions
  3. customseparate portions
  4. additionthe reaction solution was dropped to water (3,500 ml)
  5. filtrationthe precipitated solid was collected by filtration
  6. additionToluene (2,500 ml) was added
  7. dissolutionto dissolve the solid
  8. dry with materialthe solid was dried over magnesium sulfate
  9. filtrationAfter filtration
  10. concentrationthe filtrate was concentrated
  11. concentrationThe resulting concentrate
  12. additionwas dispersed
  13. washwashed by addition of n-hexane (500 ml)
  14. customdried overnight under reduced pressure

Sources & evidence

ORD record
ord-b6921b48d7c441ceacd34b1f67f5c6eb
Source dataset
uspto-grants-2015_11
Patent number
US09196839B2

Reaction notes

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