Reaction #2307968

ord-dac9856803634a629a47771f26055a76

Reaction equation

c1ccc(Nc2ccccc2)cc1
diphenylamine
CC(C)(C)[O-].[Na+]
sodium tert-butoxide
Cc1ccccc1
toluene
→
c1ccc(N(c2ccccc2)c2c3ccccc3c(-c3ccc4ccccc4c3)c3ccccc23)cc1
pure yellow product
Yield 99.0%
c1ccc(N(c2ccccc2)c2c3ccccc3c(-c3ccc4ccccc4c3)c3ccccc23)cc1
10-(2-naphthalenyl)-N,N-diphenyl-9-anthraceneamine
Yield 99.0%

Reactants

c1ccc(Nc2ccccc2)cc1
diphenylamine
CC(C)(C)[O-].[Na+]
sodium tert-butoxide
Cc1ccccc1
toluene
—
9-bromo-10-(2-naphthylenyl)anthracene

Reagents

CC(C)(C)P(C(C)(C)C)C(C)(C)C
tri-tert-butylphosphine
CC(=O)[O-].CC(=O)[O-].[Pd+2]
palladium(II) acetate

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureMixture heated
  2. 2
    Temperatureat reflux for 2 days
  3. 3
    TemperatureAfter cooling
  4. 4
    Othertoluene removed by rotary evaporation

Procedure

9-bromo-10-(2-naphthylenyl)anthracene (3.3 g, 0.008 mol), diphenylamine (1.5 g, 0.008 mol), 1.0 g sodium tert-butoxide, 0.1 g palladium(II) acetate, 3 drops tri-tert-butylphosphine and 80 ml toluene are added to a round bottom flask under a nitrogen atmosphere. Mixture heated at reflux for 2 days. After cooling, toluene removed by rotary evaporation and remaining solid chromatographer on a silica gel column to yield 4.0 g (99% yield) of pure yellow product. FD-MS (m/z): 471.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07368178B2uspto-grants-2008_05