Hydrochloric Acid → HCID 86622738, compound

To a suspension of 2-fluoro-6-(2,2,2-trifluoroethoxy)benzonitrile (2.3 g, 11 mmol, J. Hetelocyclic Chem. 1988, 25, 1173-1177) in toluene (40 mL) was added diisobutylaluminium hydride (1.0 M in toluene, 11 mL, 11 mmol) at −78° C. The mixture was warmed to room temperature and stirred for 16 h. Methanol (3.0 mL) was added to the mixture and the mixture was stirred for 10 min, then 2N hydrochloric acid (6.0 mL) was added to the mixture. After being stirred at room temperature for 1 h, the mixture was extracted with ethyl acetate (50 mL×2) and washed with aq. sodium hydrogencarbonate. The combined extracts were dried over magnesium sulfate and concentrated in vacuo to give a solid. The residual solid was purified by silica gel column chromatography (hexane/ethyl acetate 4:1) to afford 2.2 g (94%) of the title compound as a white solid.

1. stirringthe mixture was stirred for 10 min
2. stirringAfter being stirred at room temperature for 1 h
3. extractionthe mixture was extracted with ethyl acetate (50 mL×2)
4. washwashed with aq. sodium hydrogencarbonate
5. dry with materialThe combined extracts were dried over magnesium sulfate
6. concentrationconcentrated in vacuo
7. customto give a solid
8. customThe residual solid was purified by silica gel column chromatography (hexane/ethyl acetate 4:1)

ORD record

ord-6781ff8556f14fbeab41cf457d8984dd

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08816090B2