Reaction #48069

Reaction equation

3-bromo-4-fluorophenylamine

cyclopropyl boronic acid

potassium phosphate

tricyclohexyl phosphine

→

3-cyclopropyl-4-fluorophenylamine

Yield 64.0%

Solvents

toluene

water

water

Conditions

Workup

1. 1
   TemperatureThe mixture was then cooled to RT
2. 2
   Extractionextracted with ether
3. 3
   Washwashed with brine
4. 4
   Dryingdried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo
7. 7
   Otherto give a residue which
8. 8
   Otherwas purified by flash column chromatography

Procedure

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)+.

Source