Boron tribromide → 4-Chloro-5-fluoro-2-methyl-quinolin-8-ol
Reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([O:13]C)[CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([CH3:15])[CH:3]=1.B(Br)(Br)Br>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([OH:13])[CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([CH3:15])[CH:3]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
4-Chloro-5-fluoro-8-methoxy-2-methyl-quinoline (0.440 g, 1.95 mmol) was coevaporated in anhydrous toluene (2×15 mL). The residue was dissolved in anhydrous DCM (25 mL) and BBr3 (1 M in DCM, 9.8 mL, 9.8 mmol) was added dropwise at −75° C. The reaction mixture was allowed to warm to room temperature over 3.5 h. The reaction mixture was then concentrated in vacuo and the residue was partitioned between DCM (10 mL) and water (7 mL). The pH of the aqueous layer was adjusted to 8 by the addition of saturated aqueous NaHCO3 solution and the aqueous layer was extracted with DCM (2×30 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS (m/z): 212.3 [M+H+].