Cesium carbonate → HCID 18700159, compound

Temperature

0 °C

To a stirred solution of 4-nitro-2-hydroxytoluene (5 g, 33 mmol) in DMF (75 mL) at 0° C. was added 2,2,2-trifluoroethyl trifluoromethylsulfonate (13 g, 62 mmol) and Cs2CO3 (20 g, 62 mmol). The mixture was stirred at 0° C. for 30 min and then at ambient temperature for 2 h. The mixture was diluted with EtOAc (150 mL) and filtered. The filtrate solvents were removed under reduced pressure and the residue was dissolved in EtOAc (200 mL) and washed with saturated aqueous NaHCO3 (2×100 mL) and brine (50 mL). The organic phase was dried (MgSO4), filtered, and the volume was reduced to ~50 mL under reduced pressure, at which point the product had begun to crystallize. The mixture was cooled to -20° C. for 14 h, filtered, and the solids were washed with cold EtOAc. 4-Nitro-2-(2,2,2-trifluoroethoxy)toluene was obtained as a crystalline solid (HPLC retention time=10.0 min (method A)).

1. waitat ambient temperature for 2 h
2. filtrationfiltered
3. customThe filtrate solvents were removed under reduced pressure
4. dissolutionthe residue was dissolved in EtOAc (200 mL)
5. washwashed with saturated aqueous NaHCO3 (2×100 mL) and brine (50 mL)
6. dry with materialThe organic phase was dried (MgSO4)
7. filtrationfiltered
8. customto crystallize
9. temperatureThe mixture was cooled to -20° C. for 14 h
10. filtrationfiltered
11. washthe solids were washed with cold EtOAc

ORD record

ord-18181160a91b46b3bd0eb58c01ad411f

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06090805