N-bromobutanimide → 2-(1-Bromonaphthalen-2-yl)ethan-1-ol

A solution of 2-(2-hydroxy-ethyl)-naphthalene (58.5 g, 0.34 mol) in anhydrous acetonitrile (500 mL) was treated with N-bromo-succinimide (66.5 g, 0.37 mol). The resulting solution was stirred at room temperature under a nitrogen atmosphere and protected from light for 30 minutes, then heated in an oil bath at 50° C. for 2 hours. After cooling to room temperature, the reaction mixture was evaporated under vacuum to a viscous oil. The oil in diethyl ether (350 mL) was washed with water (350 mL), dilute aqueous sodium thiosulfate (300 mL), water (300 mL) and brine (200 mL), dried over magnesium sulfate, filtered, and evaporated under vacuum to an oil (89.5 g) that solidified on standing. The crude product was chromatographed on a column of EM silica gel 60, eluting with methylene chloride, to afford a yellow solid (78.2 g). Recrystallization of this material from carbon tetrachloride provided the title compound (46.5 g) as a pale yellow solid.

1. temperatureheated in an oil bath at 50° C. for 2 hours
2. temperatureAfter cooling to room temperature
3. customthe reaction mixture was evaporated under vacuum to a viscous oil
4. washThe oil in diethyl ether (350 mL) was washed with water (350 mL), dilute aqueous sodium thiosulfate (300 mL), water (300 mL) and brine (200 mL)
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. customevaporated under vacuum to an oil (89.5 g) that
8. customThe crude product was chromatographed on a column of EM silica gel 60
9. washeluting with methylene chloride

ORD record

ord-0f24e6c02ce94b8fa951bab66843376a

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06399597B1