Methyl iodide → 2-(4-Bromophenyl)propanenitrile

To a solution of 2-(4-bromophenyl)acetonitrile (5.0 g, 25.5 mmol) in anhydrous THF (70 mL) was cooled to 0° C. and sodium hydride (60 wt %, 1.5 g, 38.3 mmol) added portion wise. The mixture was stirred at room temperature for 1 h. After which methyl iodide (1.$ mL, 28.1 mmol) was added and the mixture stirred for 14 h. The reaction mixture was carefully quenched with water at 0° C. and diluted with ethyl acetate (200 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (3.8 g, 72%) as a yellow oil: ESI MS m/z 210 [C9H8BrN+H]+.

1. stirringthe mixture stirred for 14 h
2. customThe reaction mixture was carefully quenched with water at 0° C.
3. additiondiluted with ethyl acetate (200 mL)
4. customThe layers were separated
5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customthe residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane)

ORD record

ord-40de7c70dfea48b9b7262cc7dc63081f

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962648B2