Benzyl Bromide → Propanenitrile, 3-(phenylmethoxy)-

To a suspension of sodium hydride (60% dispersion in mineral oil; 14.6 g) in tetrahydrofuran (281 mL), ethylene cyanohydrin (21.0 mL) was added dropwise at 0° C. and the mixture was stirred at that temperature for 40 minutes. After adding benzyl bromide (44.4 mL) to the reaction mixture, the resulting mixture was stirred overnight as it was brought to room temperature. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, which was then extracted with ethyl acetate three times. The combined organic layers were washed with saturated brine and dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by NH silica gel column chromatography (n-hexane:ethyl acetate=100:0-70:30) to give 3-(benzyloxy)propanenitrile as a colorless oil (24.7 g).

1. additionwas added dropwise at 0° C.
2. stirringthe resulting mixture was stirred overnight as it
3. customwas brought to room temperature
4. extractionwas then extracted with ethyl acetate three times
5. washThe combined organic layers were washed with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe desiccant was removed by filtration
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe resulting residue was purified by NH silica gel column chromatography (n-hexane:ethyl acetate=100:0-70:30)

ORD record

ord-e0272204fa8642ee8d63344914011ec3

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422240B2