Reaction #674291

Reaction equation

3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridine-2-amine

NBS

→

5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine

Yield 82.5%

Solvents

CH3CN DCM

Conditions

Workup

1. 1
   OtherThe precipitate was removed by filtration
2. 2
   ConcentrationThe black filtrate was concentrated
3. 3
   Otherto give a black residue which
4. 4
   Otherwas purified by CombiFlash (80 g silica gel column, EtOAc/Hexane)

Procedure

To a solution of 3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridine-2-amine (7.49 g, 24.87 mmol) in CH3CN/DCM (100/30 mL) was added NBS (4.43 g, 24.87 mmol) in portions at 0° C. The reaction solution was stirred at 0° C. for 10 min. The precipitate was removed by filtration. The black filtrate was concentrated to give a black residue which was purified by CombiFlash (80 g silica gel column, EtOAc/Hexane) to afford 5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine (7.8 g, 82%) as a pale yellow solid.

Source