1-Bromo-4-fluorobenzene → HCID 15737986, compound

Participants

Reaction Steps

A solution of 4-fluorophenylmagnesium bromide (prepared from 7.6 ml (0.070 mol) 4-bromofluorobenzene and 3.40 g (0.14 mol) magnesium turnings) in tetrahydrofuran (150 mL) was added to a suspension of 4-(4-acetylphenyl)pyridine (9.85 g, 0.050 mol) in tetrahydrofuran (50 mL) at 0°. The mixture was stirred for 30 min at 0° and for 30 min at room temperature, then was poured into saturated aqueous ammonium chloride. The mixture was extracted with ether, the organic phase was washed with water and brine, then was dried over magnesium sulfate and concentrated. The residue was recrystallized (1-chlorobutane) to give 1-(4-fluorophenyl)-1-[4-(4-pyridyl)phenyl]ethanol colorless needles (10.0 g, 68%). MP 166-170°; NMR (CDCl3) 8.60 (d, 2H), 7.60-7.40 (8H), 7.00 (t, 2H), 2.00 (s, 3H).

Provenance & Evidence