Potassium Cyanide → (2-Fluoro-4-methoxyphenyl)acetonitrile

To a mixture of 1-Bromomethyl-2-fluoro-4-methoxy-benzene (4.5 g, 21 mmol) and Tetrabutylammonium iodide (0.66 g, 2.1 mmol) in CH2Cl2 (50 mL) was added a solution potassium cyanide (4.0 g, 60 mmol) in water (50 mL). The resulting biphasic mixture was stirred vigorously for 8 hours. The reaction was poured into water (100 mL) and extracted with CH2Cl2 (2×50 mL). The organics were washed with water (100 mL) and brine (100 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (10–30% EtOAc in hexanes) to give the product (2.6 g, 75% yield) as a clear oil. 1H NMR (300 MHz, CDCl3) δ: 3.66 (s, 2 H), 3.82 (s, 3 H), 6.69 (m, 2 H), 7.31 (m, 1 H).

1. extractionextracted with CH2Cl2 (2×50 mL)
2. washThe organics were washed with water (100 mL) and brine (100 mL)
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue was purified by flash column chromatography (10–30% EtOAc in hexanes)

ORD record

ord-9b95245d806c4c7795b9e499babab684

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07148226B2