Dimethylformamide → 4-Fluorobenzonitrile

5-FLUORO-2-(TRIFLUOROMETHYL)BENZONITRILE (compound 8h; Oakwood), K2CO3 (4 eq.) and DMF (5 mL) was shaken at 110° C. for 16 h. After cooling to room temperature, the mixture was diluted with water (20 mL), extracted with CHCl3 (3×20 mL), and concentrated. The residue was dissolved in THF/MeOH (10 mL/4 mL), and treated with HCl (1N, 3 mL) at room temperature for 12 h. The solvent was evaporated and the residue was diluted with CHCl3 (20 mL), neutralized with NH4OH (28% aqueous) and purified by column chromatography (CH3Cl/MeOH 10/1) to give:

1. extractionextracted with CHCl3 (3×20 mL)
2. concentrationconcentrated
3. dissolutionThe residue was dissolved in THF/MeOH (10 mL/4 mL)
4. additiontreated with HCl (1N, 3 mL) at room temperature for 12 h
5. customThe solvent was evaporated
6. additionthe residue was diluted with CHCl3 (20 mL)
7. custompurified by column chromatography (CH3Cl/MeOH 10/1)
8. customto give

ORD record

ord-2aa16be51f2b4889b4f1b9cb99afa292

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056832B2