Diphenylamine → 4-Methoxytriphenylamine

HRID 1247705Notes

Reaction equation

HRID 1247705 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.CC(C)([O-])C.[Na+].Cl[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.C1(C2(C3C=CC=CC=3)CC2(P(C(C)(C)C)C(C)(C)C)C)C=CC=CC=1>[C:8]1([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 11487DiphenylamineHCID 121674-ChloroanisoleHCID 23676156Sodium t-butoxide

Product 1

HCID 98820374-MethoxytriphenylamineYield 96.2%

Reagents, catalysts & solvents 2

HCID 21909131Di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphaneCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of diphenylamine (0.34 g, 2.0 mmol) in 4 ml of toluene were added sodium tert-butoxide (0.23 g, 2.4 mmol), 4-chloroanisole (0.27 ml, 2.2 mmol), (π-allyl)palladium chloride (3.7 mg, 0.01 mmol) and 2,2-diphenyl-1-(di-tert-butylphosphino)-1-methylcyclopropane (14.1 mg, 0.04 mmol) obtained in Example 4 under a nitrogen atmosphere and the mixture was stirred for 3 hours at 100° C. The reaction mixture was cooled, washed with water, and dried over anhydrous magnesium sulfate. Then, the solvent was removed under reduced pressure, and the concentrate was purified by column chromatography to give the title compound (0.53 g, 95%) as white crystal.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThen, the solvent was removed under reduced pressure
  5. customthe concentrate was purified by column chromatography

Sources & evidence

ORD record
ord-507ac0769edc47e6aaaa819acc01272a
Source dataset
uspto-grants-2006_10
Patent number
US07129367B2

Reaction notes

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