Diethyl Ether → HCID 20277029, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromofluorobenzene (87.5 g) dissolved in 1000 ml of dry ether was cooled to -20° C. and kept under dry N2.N-butyllithium (0.5 moles 15% W/V in n-hexane) was added during 1 hour while the temperature was kept below 0° C. The reaction mixture was stirred for another 1/2 h and further cooled to -30° C. 5-Methyl-3-pyridylindanone (75 g) (prepared according to the standard methods--J. Med. Chem., 11, (1968), 1064-1066) dissoled in dry ether (500 ml) was added dropwise at such a rate as to keep the temperature below -10° C. Subsequently the temperature was slowly raised to room temperature and the mixture poured into NH4Cl(100 g) in H2O (3 liters). The organic phase was separated and washed with brine, dried (MgSO4), and the solvents evaporated. Upon addition of ether (200 ml) the title compound precipitated and was filtered off. Yield: 55 g (52%). MP: 187°-192° C.

Provenance & Evidence