Hydrochloric Acid → Benzonitrile, 4-(2-methylpropyl)-3-(trifluoromethyl)-

To a solution of 4-chloro-3-(trifluoromethyl)benzonitrile (1 g) and iron(3+) tris[(2Z)-4-oxopent-2-ene-2-oleate] (86 mg), and 1-methylpyrrolidin-2-one (2.8 ml) in THF (30 ml) was added a solution of 2M bromo(isobutyl)magnesium in diethyl ether (2.9 ml) under ice-cooling. The solution was stirred at room temperature for 30 minutes, and diluted with diethyl ether (30 ml), and then 1M HCl was carefully added thereto to complete the reaction. The reaction solution was extracted with EtOAc (100 ml), and the organic layer was dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=100:0 to 95:5) to obtain 4-isobutyl-3-(trifluoromethyl)benzonitrile (320 mg) as a pale yellow liquid.

1. temperaturecooling
2. customthe reaction
3. extractionThe reaction solution was extracted with EtOAc (100 ml)
4. dry with materialthe organic layer was dried over anhydrous MgSO4
5. filtrationfiltered
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=100:0 to 95:5)

ORD record

ord-35f3128cc2f545d6bd1a970e68b86c78

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678820B2