반응 #48069

반응 방정식

3-bromo-4-fluorophenylamine

cyclopropyl boronic acid

potassium phosphate

tricyclohexyl phosphine

→

3-cyclopropyl-4-fluorophenylamine

수율 64.0%

용매

toluene

water

water

반응 조건

후처리

1. 1
   온도The mixture was then cooled to RT
2. 2
   추출extracted with ether
3. 3
   세척washed with brine
4. 4
   건조dried (MgSO4)
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타to give a residue which
8. 8
   기타was purified by flash column chromatography

실험 절차

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)+.

출처