Bromoacetonitrile → Ethyl 3-cyano-2-(4-(trifluoromethyl)phenyl)propanoate

Temperature

-78 °C

To a solution of the product from Example 266A (5.25 g, 23.0 mmol) in dry tetrahydrofuran at −78° C. was added lithium bis(trimethylsilyl)amide (1.0 M in hexane) (23.00 mL, 23.0 mmol) dropwise via syringe under nitrogen. The reaction was brought to 0° C. and stirred for one hour. The reaction was re-cooled to −78° C. and then bromoacetonitrile (1.56 mL, 23.0 mmol) was added as a solution in tetrahydrofuran (10 mL). The reaction was stirred for 2 hours while the temperature was allowed to reach room temperature. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted with diethyl ether. The organics were washed with brine, dried with MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (10% ethyl acetate/hexanes), to obtain the title compound. MS (DCI+) m/z 289 (M+NH4)+.

1. customwas brought to 0° C.
2. stirringThe reaction was stirred for 2 hours while the temperature
3. customto reach room temperature
4. customThe reaction was quenched with saturated aqueous ammonium chloride solution
5. extractionextracted with diethyl ether
6. washThe organics were washed with brine
7. dry with materialdried with MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified by silica gel chromatography (10% ethyl acetate/hexanes)

ORD record

ord-c26d5049539b4c03b932f0caef504953

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08044069B2