Hydrochloric Acid → 3-Fluoro-2-methyl-4-(trifluoromethyl)benzoic acid

25.0 g (120.1 mmol) of 3-fluoro-4-trifluoromethylbenzoic acid were dissolved in 250 ml of dry THF, and 100.9 ml (2.5M in hexane, 252.3 mmol) of n-butyllithium were added dropwise at a temperature of −40° C. The mixture was stirred for 3.5 h, and a solution of 51.2 g (360.4 mmol) of iodomethane in 50 ml of dry THF was then added. The mixture was stirred for 16 h, and after half an hour the temperature slowly increased to RT. For work-up, 150 ml of 1M HCl were added carefully. The mixture was extracted with diethyl ether, and the organic phase was then extracted with 1M NaOH. The aqueous phase was acidified and then extracted with diethyl ether. The organic phase was washed with water, dried and concentrated. The residue was triturated with n-heptane, and the solid was collected by filtration. What was isolated were 13.5 g of the pure product.

1. stirringThe mixture was stirred for 16 h
2. extractionThe mixture was extracted with diethyl ether
3. extractionthe organic phase was then extracted with 1M NaOH
4. extractionextracted with diethyl ether
5. washThe organic phase was washed with water
6. customdried
7. concentrationconcentrated
8. customThe residue was triturated with n-heptane
9. filtrationthe solid was collected by filtration
10. customWhat was isolated

ORD-Eintrag

ord-92e033f84d8748eb8609abb2ac1f7f78

Quelldatensatz

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07943551B2