反应详情

To an ice cold solution of 6-methoxy-3-methyl-1H-indazole (620 mg, 3.82 mmol) in CH2Cl2 (25 mL) was added a solution of BBr3 in CH2Cl2 (1 M, 17 mL). The ice bath was removed and the reaction was allowed to warm to room temperature and stirred overnight. The solution was carefully quenched by slowly pouring into iced saturated aqueous NaHCO3. The phases were separated and the aqueous phase was extracted with EtOAc (3×). The combined organic extracts were concentrated and the crude material was purified Biotage (40S column, 45-60% acetone/heptane) to provide 3-methyl-1H-indazol-6-ol (458 mg, 81%).

1. customThe ice bath was removed
2. customThe solution was carefully quenched
3. additionby slowly pouring into iced saturated aqueous NaHCO3
4. customThe phases were separated
5. extractionthe aqueous phase was extracted with EtOAc (3×)
6. concentrationThe combined organic extracts were concentrated
7. customthe crude material was purified Biotage (40S column, 45-60% acetone/heptane)