Toluene → HCID 59709546, compound

HRID 2220786Notes

Reaction equation

HRID 2220786 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.[CH3:14][C:15]([CH3:18])([O-])[CH3:16].[Na+].[C:20]1([CH3:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:14]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:26]=[CH:16][C:15]=1[C:18]1[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[C:26]([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:20]2[C:25]=1[CH:24]=[CH:23][CH:22]=[CH:21]2

Participants

6

Reactant 3

HCID 1140TolueneHCID 11487DiphenylamineHCID 23676156Sodium t-butoxide

Product 1

HCID 59709546HCID 59709546, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 167845palladium(II) acetateCatalyst

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.

Workup

  1. temperatureMixture heated
  2. temperatureat reflux for 2 days
  3. temperatureAfter cooling
  4. customtoluene removed by rotary evaporation

Sources & evidence

ORD record
ord-dac9856803634a629a47771f26055a76
Source dataset
uspto-grants-2008_05
Patent number
US07368178B2

Reaction notes

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