1,10-Phenanthroline → 4,4'-Dibromo-N,N-diphenyl[1,1'-biphenyl]-2-amine

HRID 11745

Reaction equation

HRID 11745 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[C:4]([NH2:15])[CH:3]=1.I[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[K+].N1[C:38]2[C:29](=[CH:30][CH:31]=[C:32]3[C:37]=2N=CC=C3)C=CC=1>C1(C)C=CC=CC=1.[Cu]Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([Br:14])=[CH:12][CH:13]=2)=[C:4]([N:15]([C:29]2[CH:38]=[CH:37][CH:32]=[CH:31][CH:30]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 11575IodobenzeneHCID 14797Potassium HydroxideHCID 45594205-Bromo-2-(4-bromophenyl)aniline

Product 1

HCID 219763174,4'-Dibromo-N,N-diphenyl[1,1'-biphenyl]-2-amineYield 835.7%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 1140TolueneSolvent2×

Procedure

4,4′-Dibromo-2-amino-1,1′-biphenyl (16.35 g, prepared according to Libman and Slack (1951) J. Chem. Soc., p. 2588), iodobenzene (26.52 g, 0.13 mol), flake potassium hydroxide (22.4 g, 0.35 mol), 1,10-phenanthroline (0.45 g), copper (I) chloride (0.25 g), and toluene (30 ml) were charged into a flask and stirred at reflux for 15 hours. The dark reaction mixture was cooled to room temperature and diluted with 200 ml of toluene. The toluene solution was washed with DI water, dried with magnesium sulfate, and evaporated. The dark residue obtained was recrystallized trice from hexane/toluene (4:1 volume) to yield 10 grams of white crystals to yield the desired monomer. 1H NMR (CDCl3): δ=6.8–7.5, multiple peaks.

Workup

  1. temperatureat reflux for 15 hours
  2. customThe dark reaction mixture
  3. washThe toluene solution was washed with DI water
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. customThe dark residue obtained
  7. customwas recrystallized trice from hexane/toluene (4:1 volume)

Sources & evidence

ORD record
ord-709f53a743134d82ad7ff2bb00604b97
Source dataset
uspto-grants-2006_08
Patent number
US07098297B2

Linked notes

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