Aniline → (4-tert-Butyl-phenyl)-phenyl-amine

HRID 1715518Notes

Reaction equation

HRID 1715518 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.N#N.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].CC([O-])=O.CC([O-])=O.[Pd+2]>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:3][CH:4]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

8

Reactant 3

HCID 6115AnilineHCID 775951-Bromo-4-tert-butylbenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 11447459(4-tert-Butyl-phenyl)-phenyl-amineYield 99.2%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 947NitrogenSolventHCID 1140TolueneSolvent

Procedure

96.4 g (452 mmol) of 1-bromo-4-tert-butylbenzene and 42.1 g (452 mmol) of aniline are dissolved in toluene and saturated with N2 for 15 min. 2.85 g (5 mmol) of DPPF, followed by 1.13 g (5 mmol) of Pd(OAc)2 and 56.8 g (588 mmol) of NaOtBu are subsequently added successively, and the mixture is refluxed for 6 h. The organic phase is separated off, washed twice with water and filtered through Celite, rinsed with toluene and evaporated in a rotary evaporator, leaving 101 g of ochre-coloured solid (99% of theory), which is employed without further purification in the subsequent reaction.

Workup

  1. additionare subsequently added successively
  2. temperaturethe mixture is refluxed for 6 h
  3. customThe organic phase is separated off
  4. washwashed twice with water
  5. filtrationfiltered through Celite
  6. washrinsed with toluene
  7. customevaporated in a rotary evaporator

Sources & evidence

ORD record
ord-63384d02642f4c8a864c899477d2ccbb
Source dataset
uspto-grants-2010_09
Patent number
US07799875B2

Reaction notes

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