Boron tribromide → 2-Methyl-1,3-benzothiazol-6-ol

To a cooled (−78° C.) solution of 6-methoxy-2-methylbenzo[d]thiazole (0.861 g, 4.80 mmol) in dichloromethane (10 mL) was added BBr3 (5 mL of 1.0 M solution in dichloromethane). After slowly warming to room temperature and stirring for 16 hours, the mixture was cooled to 0° C. and slowly quenched with methanol (20 mL). The reaction mixture was warmed to room temperature and concentrated under reduced pressure. The residue was partitioned between saturated NaHCO3 and dichloromethane/isopropyl alcohol (85/15). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to provide the crude product (0.351 g, 44%) that was used without further purification.

1. temperaturethe mixture was cooled to 0° C.
2. customslowly quenched with methanol (20 mL)
3. temperatureThe reaction mixture was warmed to room temperature
4. concentrationconcentrated under reduced pressure
5. customThe residue was partitioned between saturated NaHCO3 and dichloromethane/isopropyl alcohol (85/15)
6. dry with materialThe organic layer was dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-33b628fc50b2431cbbc37ee7eb720c52

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08648087B2