Reaction #84057

Reaction equation

Methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoate

BBr3

H2O

→

Compound 1

Yield 28.1%

4-(6-hydroxy-3-methylquinolin-2-yl)benzoic acid

Yield 28.1%

Solvents

DCM

Conditions

Workup

1. 1
   workup.STIRRINGThe solution was stirred vigorously for 1 h
2. 2
   Filtrationfollowed by filtration of the solids
3. 3
   WashThe solids were washed with H2O
4. 4
   Otherdried in vacuo

Procedure

Methyl 4-(6-methoxy-3-methylquinolin-2-yl)benzoate (37 mg, 0.121 mmol) was dissolved in 2 mL of DCM and BBr3 (150 μL) was added. The mixture was stirred at room temperature for 1 day followed by addition of 10 mL of H2O. The solution was stirred vigorously for 1 h followed by filtration of the solids. The solids were washed with H2O and dried in vacuo to yield 9.5 mg (28% yield) of Compound 1. 1H NMR (DMSO-d6, 400 MHz): δ 8.37 (s, 1H), 8.10 (d, 2H), 7.94 (d, 1H), 7.78 (d, 2H), 7.42-7.39 (dd, 1H), 7.24-7.23 (d, 1H), 2.43 (s, 3H). MS (ESI): m/z 280.10 [M+H]+.

Source