3-Methoxy-5-nitrobenzotrifluoride → 3-Hydroxy-5-nitrobenzotrifluoride

Temperature

200 °C

To a solution of 1-methoxy-3-nitro-5-(trifluoromethyl)benzene (1.0 g, 4,5 mmol) in dichloromethane (10 ml) was added pyridine hydrochloride salt (4.0 g, 35 mmol). After addition dichloromethane was removed under vacuum and the resulting solid mixture was heated at 200° C. overnight in an open reaction flask. After cooling to RT, 10% HCl (50 ml) was added and the mixture was extracted with EtOAc (3×50 ml). The combined organic layer was washed with brine (50 ml) and dried over Na2SO4. Solvent was removed under vacuum and the residue was purified by flash column chromatography on the silica gel (hexane/EtOAc=3:1) to afford the title compound as a white solid.

1. customwas removed under vacuum
2. temperatureAfter cooling to RT
3. addition10% HCl (50 ml) was added
4. extractionthe mixture was extracted with EtOAc (3×50 ml)
5. washThe combined organic layer was washed with brine (50 ml)
6. dry with materialdried over Na2SO4
7. customSolvent was removed under vacuum
8. customthe residue was purified by flash column chromatography on the silica gel (hexane/EtOAc=3:1)

ORD record

ord-eaf4e0c21fc74c92a586daf6d58ed2ed

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07880000B2