Boron tribromide → 3-Amino-2-chloro-4-fluorophenol
Reaction equation
[Cl:1][C:2]1[C:8]([O:9]C)=[CH:7][CH:6]=[C:5]([F:11])[C:3]=1[NH2:4].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:4][C:3]1[C:2]([Cl:1])=[C:8]([OH:9])[CH:7]=[CH:6][C:5]=1[F:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-chloro-6-fluoro-3-methoxy-aniline (0.85 g, 4.84 mmol, 1.0 eq) in DCM (8 mL) at 0° C. was added BBr3 (6.06 g, 24.2 mmol, 5.0 eq). The mixture was stirred at room temperature under N2 overnight, then poured into ice-water. The pH of the solution was adjusted to pH 6 by addition of sat.NaHCO3. The dichloromethane was removed under reduced pressure and the aqueous residue was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a pale yellow solid (0.74 g, 95%).