Potassium Phosphate, Tribasic → 3-Cyclopropyl-4-fluoroaniline

Temperatur

100 °C

To a solution of 3-bromo-4-fluorophenylamine (synthesized as described in J. Org. Chem. 1981, 46, 2280-2286) (415 mg, 2.18 mmol), cyclopropyl boronic acid (244 mg, 2.84 mmol), potassium phosphate (1.62 g, 7.64 mmol), and tricyclohexyl phosphine (61 mg, 0.22 mmol) in toluene (10 ml) and water (0.5 ml) was added palladium acetate (25 mg, 0.11 mmol) and the reaction mixture was heated to 100° C. overnight. The mixture was then cooled to RT and diluted with water and extracted with ether. The organic phases were combined, washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography to give 3-cyclopropyl-4-fluorophenylamine (210 mg, 64%). MS (ISP) 152.2 (M+H)+.

1. temperatureThe mixture was then cooled to RT
2. extractionextracted with ether
3. washwashed with brine
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give a residue which
8. customwas purified by flash column chromatography

ORD-Eintrag

ord-14b57bd0666e45aab253ce6c60b843fa

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07745477B2