Benzyl Bromide → HCID 10957810, compound

Temperature

20 °C

To a cold (−78° C.) solution of diisopropyl-(R)-(+)-malate (9.4 mL; 45.82 mmol; 1.00 eq.) in anhydrous THF (17 mL) was added slowly a solution (1 M) of lithium bis(trimethylsilyl)amide (96.2 mL; 1.00 M; 96.2 mmol; 2.10 eq.) in THF. The temperature was raised to 20° C. over 30 minutes, than lowered again to −78° C. Benzyl bromide (9.40 g; 55.0 mmol; 1.20 eq.) was added and the mixture stirred at RT for 16 hours. The reaction mixture was then cooled to 0° C. and a saturated solution of NH4Cl was added. The resulting mixture was diluted with water, extracted three times with EtOAc. The combined organic layers were washed with brine and dried over MgSO4, filtered and evaporated under reduced pressure. The residue was then purified by chromatography (SiO2, 20/80 EtOAc/c-hex) to give the product as a colourless oil (9.76 g, 69%).

1. customthan lowered again to −78° C
2. temperatureThe reaction mixture was then cooled to 0° C.
3. extractionextracted three times with EtOAc
4. washThe combined organic layers were washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated under reduced pressure
8. customThe residue was then purified by chromatography (SiO2, 20/80 EtOAc/c-hex)

ORD record

ord-97776c84bf0e496fa93bd0f9e4be8c94

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247437B2