Methyl iodide → 2-(3,4-Dichlorophenyl)propanenitrile

Temperature

-78 °C

To a −78° C. solution of (3,4-dichloro-phenyl)-acetonitrile (5.0 g, 26.9 mmol) in THF (60 mL) was added LHMDS (1 M in THF, 28.2 mL, 28.2 mmol). The reddish orange solution was stirred at −78° C. for 1 h and MeI (1.76 mL, 28.2 mmol) was added. The mixture was allowed to warm to rt overnight. The mixture was diluted with 1 M HCl (20 mL) and extracted with Et2O (3×). The combined organic layers were dried (MgSO4) and concentrated to provide a dark brown oil. The crude product was purified by flash chromatography (hexanes/EtOAc) to provide a colorless oil (5.0 g, 93%). 1H NMR (400 MHz, CDCl3): 7.52-7.42 (m, 2H), 7.25-7.18 (m, 1H), 3.88 (q, J=7.3, 1H), 1.64 (d, J=7.3, 3H).

1. temperatureto warm to rt overnight
2. extractionextracted with Et2O (3×)
3. dry with materialThe combined organic layers were dried (MgSO4)
4. concentrationconcentrated
5. customto provide a dark brown oil
6. customThe crude product was purified by flash chromatography (hexanes/EtOAc)

ORD record

ord-e1391a5497494e41bc0637ff4531caaa

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07855292B2