Hydrochloric Acid → 4-(4-Fluorophenyl)-4-hydroxy-1-phenylcyclohexanecarbonitrile

Temperatur

-70 °C

8.8 g of 1-bromo-4-fluorobenzene were dissolved in 50 ml of dry THF in a dried two-necked flask under an argon atmosphere, cooled to −70° C., and 32.2 ml of n-butyllithium solution (1.55 M in n-hexane) were slowly added dropwise so that the internal temperature did not exceed −65° C. The reaction mixture was stirred for 1 h at −70° C. Subsequently, 10.0 g of 4-oxo-1-phenylcyclohexanecarbonitrile in the form of a suspension in 50 ml of THF were slowly added dropwise so that the internal temperature did not exceed −65° C. The reaction solution was stirred further for 1 h at −70° C. and subsequently warmed to room temperature. It was stirred for 3 h at room temperature, the reaction mixture was added to ice water, cautiously acidified with 1 N hydrochloric acid and extracted three times with EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. The crude product, a brown oil, was crystallized from toluene. 13.8 g of the title compound were obtained as a white solid.

1. customdid not exceed −65° C
2. customdid not exceed −65° C
3. stirringThe reaction solution was stirred further for 1 h at −70° C.
4. temperaturesubsequently warmed to room temperature
5. stirringIt was stirred for 3 h at room temperature
6. extractionextracted three times with EA
7. dry with materialThe combined organic phases were dried over magnesium sulfate
8. customthe solvent was removed in vacuo
9. customThe crude product, a brown oil, was crystallized from toluene

ORD-Eintrag

ord-a175e400d34f49a0ab5ba8d6ba053b73

Quelldatensatz

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08076324B2