1,3-Dibromobenzene → 3-Bromo-N,N-diphenylaniline

HRID 716593Notes

Reaction equation

HRID 716593 reaction equation
[C:1]1([NH:7][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[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[N:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 79271,3-DibromobenzeneHCID 11487DiphenylamineHCID 23676156Sodium t-butoxide

Product 1

HCID 162178513-Bromo-N,N-diphenylanilineYield 78.1%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Diphenylamine (9 g, 53.3 mmol), and 1,3-dibromobenzene (25 g, 106.8 mmol) were mixed in toluene (500 mL). The solution was bubbled nitrogen while stirring for 15 min. Pd(OAc)2 (0.18 g, 0.8 mmol), triphenylphosphine (0.84 g, 3.2 mmol) and tBuONa (7.7 g, 80.2 mmol) were added in sequence. The mixture was heated to reflux overnight under nitrogen. After cooling, the reaction mixture was filtered through Celite®/silica pad and the solvent was then evaporated. The residue was purified by column using hexane as eluent to obtain 13.5 g (60%) of 3-bromo-N,N-diphenylaniline.

Workup

  1. customThe solution was bubbled nitrogen
  2. temperatureThe mixture was heated
  3. temperatureto reflux overnight under nitrogen
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was filtered through Celite®/silica pad
  6. customthe solvent was then evaporated
  7. customThe residue was purified by column

Sources & evidence

ORD record
ord-708c4296c60045d7afdf6423e8e4a2a8
Source dataset
uspto-grants-2015_11
Patent number
US09190623B2

Reaction notes

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