Benzyl Bromide → HCID 21913792, compound

Benzyltrimethylammonium chloride (4.61 g, 24.8 mmol) was added to a mixture of tert-butyl 2-hydroxyethylcarbamate (40.0 g, 248 mmol), dichloromethane (600 mL), and 50% aqueous sodium hydroxide (400 mL). Benzyl bromide (29.5 mL, 248 mmol) was then added, and the reaction was stirred for three hours. Ice water was added (1 L), and the aqueous solution was extracted with chloroform (5×). The combined organic solutions were washed with water (2×) and brine (3×), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Upon concentration, a white precipitate formed, and the organic solution was washed again with water (3×100 mL). The combined washings were extracted with chloroform (3×50 mL). The combined organic solutions were washed with brine (3×50 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 59.1 g of tert-butyl 2-(benzyloxy)ethylcarbamate as a colorless oil.

1. extractionthe aqueous solution was extracted with chloroform (5×)
2. washThe combined organic solutions were washed with water (2×) and brine (3×)
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. concentrationUpon concentration
7. customa white precipitate formed
8. washthe organic solution was washed again with water (3×100 mL)
9. extractionThe combined washings were extracted with chloroform (3×50 mL)
10. washThe combined organic solutions were washed with brine (3×50 mL)
11. dry with materialdried over magnesium sulfate
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure

ORD record

ord-0d4e2689ee2b45e7bee19d1e1a5c651d

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07220758B2