Bromide ion → 4-Methoxy-4'-methyldiphenylamine

HRID 1282475Notes

Reaction equation

[C:1]1([CH3:8])[CH:6]=[CH:5][C:4](Br)=[CH:3][CH:2]=1.[Br-].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1.CC(C)([O-])C.[Na+].C1(C(C2C=CC=CC=2)=C(P(C2CCCCC2)C2CCCCC2)C)C=CC=CC=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:4]2[CH:5]=[CH:6][C:1]([CH3:8])=[CH:2][CH:3]=2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Into a reactor were introduced 0.330 g (1.93 mmol) of p-tolyl bromide and 4 mL of toluene under a nitrogen atmosphere. The bromide was dissolved in the solvent. To this solution were added 0.266 g (2.16 mmol) of p-anisidine, 0.226 g (2.35 mmol) of sodium t-butoxide, 8.5 mg (1 mol % based on the amine) of tris(dibenzylidene)dipalladium, and 32.3 mg (2 mmol % based on the amine) of the 1,1-diphenyl-2-(dicyclohexylphosphino)propene obtained in Example 2. The resultant reaction mixture was stirred at 100° C. for 5 hours and then cooled. Saturated aqueous ammonium chloride solution was added thereto, and this mixture was extracted with toluene. The extract was dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was purified by column chromatography to obtain 0.366 g (89%) of N-p-methoxyphenyl-N-p-tolylamine. The results obtained are shown in Table 20.

Workup

customThe resultant reaction mixture
temperaturecooled
extractionthis mixture was extracted with toluene
dry with materialThe extract was dried with anhydrous magnesium sulfate
customThereafter, the solvent was removed under reduced pressure
customThe concentrate was purified by column chromatography

Sources & evidence

ORD record: ord-bb102e8bbf7a4f1e9b411276714d84a0
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455720B1

Reaction notes

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