4-Bromobiphenyl → HCID 9817140, compound

Participants

Reaction Steps

A solution of 4-bromobiphenyl (11.8 g) in dry tetrahydrofuran (60 ml) and bromine (3 drops) were added to stirred magnesium turnings (1.18 g) and the mixture heated under reflux for 70 minutes. A solution of quinuclidin-3-one (3.65 g) in dry tetrahydrofuran (25 ml) was added dropwise to the mixture at 10° C. and the reaction mixture heated under reflux for 90 minutes. Aqueous ammonium chloride (14 g in 56 ml of water) was added dropwise to the mixture and the mixture extracted with diethyl ether. The ether extract was dried (Na2SO4) and evaporated to give a residue which was crystallised from ethyl acetate to give 3-(biphenyl-4-yl)-3-hydroxyquinuclidine (1.4 g) as a colourless solid, m.p. 180°-182° C., microanalysis, found: C, 81.7; H, 7.5; N, 5.0%; C19H21NO requires: C, 81.8; H, 7.5; N, 5.0%. This material was identical to that in Example 1 except that it was a higher melting polymorphic form.

Provenance & Evidence