1-Bromo-4-fluorobenzene → HCID 20141784, compound

Participants

Reaction Steps

n-Butyllithium (3.5 cm3 of a 1.43M solution in n-hexane) was added dropwise to a stirred solution of 4-bromo-fluorobenzene (0.88 g) in tetrahydrofuran (THF) (20 cm3) at -70° under nitrogen. After 0.5 hours a solution of anhydrous zinc chloride (0.68 g) in THF (10 cm3) was added dropwise, and the mixture was warmed to room temperature over 1 hour. 6-(4-Iodo-2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone (0.37 g) and tetrakis(triphenylphosphine)palladium (O) (0.01 g) were added and the mixture heated under reflux for 1.5 hours. The cooled solution was quenched with water (10 cm3) and poured into a saturated solution of ethylenediaminetetraacetic acid disodium salt in water (30 cm3), which had been adjusted to pH 9 by addition of sodium carbonate solution. This mixture was extracted with dichloromethane (3×100 cm3) and the combined and dried (MgSO4) extracts were evaporated in vacuo to give a residue which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with methanol:dichloromethane, 1:19 by volume. Collection and evaporation of appropriate fractions afforded a solid which was recrystallised from ethyl acetate to give the title compound, m.p. 289°-291° (0.14 g).

Provenance & Evidence