[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12]C)[C:8](=[O:14])[NH:7][CH2:6][CH2:5]2.B(Br)(Br)Br.O.CCOC(C)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[C:8](=[O:14])[NH:7][CH2:6][CH2:5]2
To a 0° C. solution of 6-fluoro-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (Cpd M, 0.428 g, 2.19 mmol) in DCM (15 mL) was added boron tribromide (1.0M in DCM, 6.00 mL, 6.00 mmol). The reaction mixture was stirred for 1 hour, then the reaction mixture was allowed to warm to room temperature. After stirring for 4 hours, water (25 mL) and EtOAc (100 mL) were added and the mixture was stirred vigorously. The layers were separated, and the organic layer was filtered and concentrated under vacuum to give 6-fluoro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (Cpd N, 355 mg, 89%).
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