Water → 2-Iodo-4-(trifluoromethyl)benzonitrile

Temperature

0 °C

Potassium iodide (5.6 g, 34 mmol) and sodium nitrite (2.4 g, 35 mmol) were added to a solution of 2-amino-4-trifluoromethyl-benzonitrile (2.58 g, 14 mmol) in acetonitrile (60 mL). The resultant mixture was cooled to 0° C. in an ice-water bath with magnetic stirring. Ice-cold concentrated HCl (14 mL) was added slowly drop-wise to the reaction mixture, causing the reaction mixture to become cloudy and deep red in color. The reaction mixture was stirred at 0° C. for 30 minutes, then warmed to room temperature. Stirring at room temperature proceeded for 3 hours. The reaction mixture was poured into water, and the resulting suspension was extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered, and concentrated to give a purple liquid. A solution of this crude product and dichloromethane (200 mL) was evaporated onto silica gel, and the dry silica gel-supported product was loaded onto a silica gel column. Manual flash chromatography using 5% ethyl acetate in hexanes afforded 2-iodo-4-trifluoromethyl-benzonitrile as 3.58 g (87%) of a purple, crystalline solid.

1. temperaturewarmed to room temperature
2. stirringStirring at room temperature
3. waitproceeded for 3 hours
4. extractionthe resulting suspension was extracted with ethyl acetate
5. dry with materialThe organic layer was dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customto give a purple liquid
9. customA solution of this crude product and dichloromethane (200 mL) was evaporated onto silica gel

ORD record

ord-45ed33349191439b91b7e6cd06ba030d

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08124629B2