2,2,2-Trifluoroethanol → HCID 54370116, compound

Temperature

-10 °C

A solution of trifluoroethanol (88 g, 64 mL, 88 mol) was added to a slurry of potassium tert-butoxide (98.8 g, 0.88 mol) in 1,2-dimethoxyethane (145 mL) such that the reaction temperature remained below 11° C. The mixture then was cooled 1.5 hours at 0° to 5° C. and added over 2.5 hours to a solution of 2,4-difluoronitrobenzene (135 g, 0.85 mol) in 1,2-dimethoxyethane (150 mL) at -10° C. The mixture was cooled 1 hour at -10° C. and then aqueous potassium dihydrogen phosphate solution (13 g, 130 mL) was added. The mixture was warmed to 25° C. and solid potassium dihydrogen phosphate (7 g) was added. The mixture was diluted with methyl tert-butyl ether (600 mL) and water (300 mL) and the organic layer was separated, diluted with methyl tert-butyl ether (100 mL), washed with water (2×400 mL), filtered through Celite (2 g) and concentrated in vacuo to give 4-fluoro-2-(2,2,2-trifluoroethoxy)nitrobenzene (13 g, 57.2 mmol)

1. customremained below 11° C
2. temperatureThe mixture then was cooled 1.5 hours at 0° to 5° C.
3. temperatureThe mixture was warmed to 25° C.
4. customthe organic layer was separated
5. additiondiluted with methyl tert-butyl ether (100 mL)
6. washwashed with water (2×400 mL)
7. filtrationfiltered through Celite (2 g)
8. concentrationconcentrated in vacuo

ORD record

ord-71557a01dc0248ffb3c6280d34004d1f

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05859014