Hydrochloric Acid → 3-Chloro-5-methoxybenzonitrile

Temperature

0 °C

To a 250 mL round bottom flask charged with 3,5-dichlorobenzonitrile (42; 7.31 g; 34.90 mmol) and maintained under an argon atmosphere was added DMF (70 mL). The flask was cooled to 0° C. and powdered sodium methoxide (1.88 g; 34.90 mmol) was added in two portions 15 min apart. The homogeneous mixture was allowed to warm to room temperature and stirred for 24 h. The solution was cooled to 0° C. and aqueous 10% HCl (20 mL) was added dropwise via an addition funnel after which the reaction was warmed to RT. The mixture was extracted with EtOAc and the combined extracts washed sequentially with water and brine. The organic phase was dried (Na2SO4), filtered, and volatile solvents were removed in vacuo. The resulting solid was recrystallized from hexanes to afford 3-chloro-5-methoxybenzonitrile (43, 4.2 g; 72%).

1. temperaturemaintained under an argon atmosphere
2. temperatureto warm to room temperature
3. temperatureThe solution was cooled to 0° C.
4. temperaturewas warmed to RT
5. extractionThe mixture was extracted with EtOAc
6. washthe combined extracts washed sequentially with water and brine
7. dry with materialThe organic phase was dried (Na2SO4)
8. filtrationfiltered
9. customvolatile solvents were removed in vacuo
10. customThe resulting solid was recrystallized from hexanes

ORD record

ord-cd282b46ea2a4b6493de063b54c21fd9

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07608731B2