Propionitrile → 3-(4-Nitrophenyl)propionitrile

Temperature

-100 °C

To a mixture of 4-nitrobenzyl alcohol (37) (1 g, 6.53 mmol) and (cyanomethyl)trimethylphosphonium iodide (36) (4 g, 16.32 mmol) were added propionitrile (32 mL) and diisopropylethylamine (2.5 g, 19.58 mmol) at room temperature. The mixture was heated at −100° C. for 24 hours. The reaction was quenched with water (1 mL), followed by addition of concentrated HCl (5 mL). The resulting reaction mixture was extracted with ethyl acetate (3×100 mL), washed with brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give a dark brown solid. The crude solid product was purified by flash column chromatography (silica gel, ethyl acetate:hexanes 1:1) to give 740 mg of 3-(4-nitrophenyl)propionitrile (38) as a light orange solid. 1H NMR (DMSO-d6): δ 8.20-8.17 (dd, J=8.7 Hz, 2H), 7.59-7.56 (d, J=9.0 Hz, 2H), and 3.06-3.01 (m, 2H).

1. customThe reaction was quenched with water (1 mL)
2. additionfollowed by addition of concentrated HCl (5 mL)
3. customThe resulting reaction mixture
4. extractionwas extracted with ethyl acetate (3×100 mL)
5. washwashed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customto give a dark brown solid
9. customThe crude solid product was purified by flash column chromatography (silica gel, ethyl acetate:hexanes 1:1)

ORD record

ord-f3542692a85649c6b12c1ea063db21cf

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815848B2