Ethyl bromoacetate → HCID 54389077, compound

Combined phenylacetonitrile (5.85 g, 50.0 mmol) and THF (30 mL). Cooled in a dry-ice/acetone bath. Added dropwise, sodium bis-(trimethylsilyl)amide (100 mL, 1.0M in THF, 100 mmol, 2 eq.). After the addition was complete, allowed to warm to ambient temperature. Cooled in a dry-ice/acetone bath. Added dropwise, ethyl bromoacetate (11 mL, 99 mmol). After the addition was complete, warmed to ambient temperature and stir for 3 h. Partitioned the reaction mixture between diethyl ether (200 mL) and water (200 mL). The organic layer was extracted with H2O (3×150 mL), 1N HCl (2×100 mL), 5% NaHCO3 (2×100 mL), and brine (1×150 mL). Dried over MgSO4, filtered, and concentrated in vacuo to obtain a residue. Chromatographed on silica gel eluting with 20% ethyl acetate in hexane to obtain the title compound:

1. temperatureCooled in a dry-ice/acetone bath
2. additionAdded dropwise
3. additionAfter the addition
4. temperatureCooled in a dry-ice/acetone bath
5. additionAdded dropwise
6. additionAfter the addition
7. temperaturewarmed to ambient temperature
8. customPartitioned the reaction mixture between diethyl ether (200 mL) and water (200 mL)
9. extractionThe organic layer was extracted with H2O (3×150 mL), 1N HCl (2×100 mL), 5% NaHCO3 (2×100 mL), and brine (1×150 mL)
10. dry with materialDried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customto obtain a residue
14. customChromatographed on silica gel eluting with 20% ethyl acetate in hexane

ORD record

ord-2d48a747b35b4522b6c4007bad8e2c38

Source dataset

uspto-grants-1997_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05635510