Boron tribromide → 2-Hydroxy-4-(methylsulfanyl)benzoic acid

Temperature

-65 °C

2-Methoxy-4-(methylthio)benzoic acid (1.002 g, 5.05 mmol) was dissolved in dichloromethane (18 mL). The solution was cooled to −65° C. in a dry ice/chloroform bath. A dichloromethane solution of boron tribromide (5.4 mL, 5.4 mmol) was then added slowly. After 3 hours, the reaction was quenched with water (5 mL) and 1 N HCl (10 mL). After stirring for 10 minutes, the reaction was extracted with dichloromethane (100 mL). The organic layer was washed with 1 N HCl (10 mL) and then dried over magnesium sulfate, filtered, and concentrated to give the pure product as a pale yellow solid (866 mg, 4.70 mmol, 93%).

1. customthe reaction was quenched with water (5 mL) and 1 N HCl (10 mL)
2. extractionthe reaction was extracted with dichloromethane (100 mL)
3. washThe organic layer was washed with 1 N HCl (10 mL)
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-88c71704ccc74fbfa80f04333ffe13e0

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700628B2