Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.C([Li])CCC.[O:14]=[C:15]1[CH2:20][CH2:19][C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:21]#[N:22])[CH2:17][CH2:16]1.Cl>C1COCC1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]2([OH:14])[CH2:20][CH2:19][C:18]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)([C:21]#[N:22])[CH2:17][CH2:16]2)=[CH:3][CH:4]=18.8 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.
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