Acetonitrile → 3-(3-Bromophenyl)-3-hydroxypropanenitrile

Temperature

-50 °C

To a cold (−50° C.) stirred solution of potassium tert-butoxide (1M/THF, 703 mL, 703 mmol) under argon was added CH3CN (27.73 g, 675.6 mmol) via syringe over 5 min and the reaction mixture was stirred at −50° C. for 30 min. Then a solution of 3-bromobenzaldehyde (22) (100 g, 540.5 mmol) was added over 5 min. The reaction mixture was stirred for 30 min at −50° C. and allowed to warm to room temperature. Aqueous NH4Cl (25%, 250 mL) was added, the mixture was stirred and layers were separated. Organic layer was washed with saturated brine (200 mL), dried over anhydrous Na2SO4, filtered, the filtrate was concentrated under reduced pressure and the residue was dried in vacuum overnight to give hydroxynitrile 23 as a pale yellow oil. Yield (117.6 g, 96%); 1H NMR (400 MHz, DMSO-d6) δ 7.60 (t, J=1.6 Hz, 1H), 7.46 (ddd, J=7.6, 2.0, 1.2 Hz, 1H), 7.40 (dd, J=7.6, 2.0 Hz, 1H), 7.31 (t, J=7.6 Hz, 1H), 6.05 (d, J=4.8 Hz, 1H), 2.94-2.80 (m, 2H).

1. stirringThe reaction mixture was stirred for 30 min at −50° C.
2. temperatureto warm to room temperature
3. stirringthe mixture was stirred
4. customlayers were separated
5. washOrganic layer was washed with saturated brine (200 mL)
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationthe filtrate was concentrated under reduced pressure
9. customthe residue was dried in vacuum overnight

ORD record

ord-f633451260b243aaa146be547cbbdf50

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08766007B2