1,10-Phenanthroline → 4,4'-Dibromotriphenylamine

HRID 2236063

Reaction equation

HRID 2236063 reaction equation
[CH:1]1[C:6]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[CH:5][CH:4]=[C:3]([Br:15])[CH:2]=1.I[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[OH-].[K+]>Cl[Cu].C1(C)C=CC=CC=1>[CH:17]1[CH:22]=[CH:21][C:20]([N:7]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)[C:6]2[CH:1]=[CH:2][C:3]([Br:15])=[CH:4][CH:5]=2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 11575IodobenzeneHCID 14797Potassium HydroxideHCID 629950Bis(4-bromophenyl)amine

Product 1

HCID 135947074,4'-Dibromotriphenylamine

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
130 °C

Procedure

In an oxygen-free glovebox, a 250 mL flask was charged with 4,4′-dibromodiphenylamine (15.0 g, 45.8 mmol), iodobenzene (18.7 g, 91.7 mmol), 1,10-phenanthroline (0.827 g, 4.59 mmol), CuCl (0.454 g, 4.59 mmol), KOH (15.4 g, 275 mmol), and toluene (125 mL). The flask was sealed and removed from the glovebox and heated to 130° C. and stirred for 24 hr. The flask was then removed from the oil bath and allowed to cool to room temperature. The solids were filtered off and the solvent was removed to yield a bluish oily substance, which was passed through silica gel column using toluene as the eluant. The fractions were collected and the solvent was removed followed by vacuum distillation at 160° C. for 30 min to remove the remaining iodobenzene to afford a blue solid. This solid was further purified by a second silica plug column using hexanes as the eluant. The colorless clear fractions were combined and the solvent removed to yield the desired product. Purity: 99+%.

Workup

  1. customThe flask was sealed
  2. customremoved from the glovebox
  3. customThe flask was then removed from the oil bath
  4. temperatureto cool to room temperature
  5. filtrationThe solids were filtered off
  6. customthe solvent was removed
  7. customto yield a bluish oily substance, which
  8. customThe fractions were collected
  9. customthe solvent was removed
  10. distillationfollowed by vacuum distillation at 160° C. for 30 min
  11. customto remove the remaining iodobenzene
  12. customto afford a blue solid
  13. customThis solid was further purified by a second silica plug column
  14. customthe solvent removed

Sources & evidence

ORD record
ord-3c668fb43c824d969da6183007a60f23
Source dataset
uspto-grants-2010_05
Patent number
US07714099B2

Linked notes

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