Methyl iodide → 2-(4-Bromophenyl)propanenitrile

To a stirred solution of 2-(4-bromo phenyl) acetonitrile (20 g, 102.04 mmol) in dry tetrahydrofuran (200 mL) was added sodium bis(trimethylsilyl)amide (18.71 g, 102.04 mmol) at 0° C. under a nitrogen atmosphere. After stirring for 20 minutes at room temperature, methyl iodide (14.48 g, 102 mmol) was added and then stirred for 1 h at room temperature. The reaction mixture was quenched with an aqueous ammonium chloride solution and extracted with ethyl acetate (2×150 mL). The combined organic layers were washed with water (2×100 mL), a saturated aqueous sodium chloride solution (2×25 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (3-4% ethyl acetate/hexanes) afforded 2-(4-bromo-phenyl)-propionitrile as a light yellow liquid (11.5 g, 53.6%).

1. stirringstirred for 1 h at room temperature
2. customThe reaction mixture was quenched with an aqueous ammonium chloride solution
3. extractionextracted with ethyl acetate (2×150 mL)
4. washThe combined organic layers were washed with water (2×100 mL)
5. dry with materiala saturated aqueous sodium chloride solution (2×25 mL), dried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-6424866992f344d2bdc5efe5cec9a5e0

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722661B2