1,10-Phenanthroline → 4-Bromo-4',4''-dimethyltriphenylamine

HRID 2256503Notes

Reaction equation

HRID 2256503 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1.N1[C:30]2[C:21](=[CH:22][CH:23]=[C:24]3[C:29]=2N=CC=C3)[CH:20]=CC=1.[OH-].[K+]>C1(C)C(C)=CC=CC=1>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([N:14]([C:24]2[CH:29]=[CH:30][C:21]([CH3:20])=[CH:22][CH:23]=2)[C:13]2[CH:15]=[CH:16][C:10]([Br:9])=[CH:11][CH:12]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 13181,10-PhenanthrolineHCID 78074-BromoanilineHCID 122074-IodotolueneHCID 14797Potassium Hydroxide

Product 1

HCID 111427014-Bromo-4',4''-dimethyltriphenylamineYield 425.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
100 °C

Procedure

In a 500 milliliter three-necked flask equipped with a mechanical stirrer, thermometer and Dean-Stark trap, all under an argon atmosphere, were added molten p-iodotoluene (27.3 grams, 125 millimoles), 22 grams of xylene, p-bromoaniline (8.7 grams, 50 millimoles), and 1,10-phenanthroline (1.8 grams, 10 millimoles). The reaction mixture was then heated to 100° C. at which point potassium hydroxide flake (22.4 grams, 400 millimoles) and cuprous chloride (1 gram, 10 millimoles) were added. The temperature was then adjusted to 125° C., and the reaction progress monitored by high performance liquid chromatography. Analysis showed the reaction to be 94 percent complete at 2 hours and 98 percent complete at 5 hours at which point the reaction was terminated. Product isolation was accomplished by adding 24 grams of acetic acid, and partitioning the reaction mixture between 100 grams of toluene and 100 grams of deionized water. The organic phase was further washed several times with deionized water, and the solvent removed to afford 15 grams (84.5 percent) of the desired product of high purity (HPLC, 98 area percent).

Workup

  1. customIn a 500 milliliter three-necked flask equipped with a mechanical stirrer
  2. additionwere added
  3. customwas then adjusted to 125° C.
  4. customthe reaction
  5. customcomplete at 2 hours
  6. customthe reaction was terminated
  7. additionby adding 24 grams of acetic acid
  8. custompartitioning the reaction mixture between 100 grams of toluene and 100 grams of deionized water
  9. customthe solvent removed

Sources & evidence

ORD record
ord-922b37b482064118ab13a8d81f08c150
Source dataset
uspto-grants-1997_08
Patent number
US05654482

Reaction notes

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