2-Aminobiphenyl → N-(2-Methoxyphenyl)[1,1'-biphenyl]-2-amine

Temperature

110 °C

Trisdibenzylideneacetonedipalladium (0.276 g, 0.3 mmol) and tri-tert-butylphosphine (0.121 g, 0.6 mmol) were put into a flask, and then dissolved in 40 mL of toluene. Subsequently, 2-biphenylamine (2.53 g, 15 mmol), 1-bromo-2-methoxybenzene (2.81 g, 15 mmol) and tert-butoxy sodium (2.16 g, 22.5 mmol) were added into the flask, and then refluxed at a temperature of 110° C. for 12 hours. After cooling the flask including the reactant mixture to room temperature, the reactant mixture was washed using an ammonium chloride aqueous solution (150 mL) to separate an organic layer. The separated organic layer was washed with distilled water three times, and was then dried with magnesium sulfate. Thereafter, residues from which volatile components were removed at reduced pressure were purified using a silica gel chromatography tube in a mixed solvent of hexane and ethylacetate (1:10), and were then recrystallized in normal hexane to produce 3.39 g of N-(2′-methoxyphenyl)biphenyl-2-amine.

1. temperatureAfter cooling the flask
2. customto room temperature
3. washthe reactant mixture was washed
4. customto separate an organic layer
5. washThe separated organic layer was washed with distilled water three times
6. dry with materialwas then dried with magnesium sulfate
7. customThereafter, residues from which volatile components were removed at reduced pressure
8. customwere purified
9. customwere then recrystallized in normal hexane

ORD record

ord-e918e3ab32194376914d423e3d58f7aa

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08742043B2