Benzyl Bromide → HCID 19418985, compound

Participants

Reaction Conditions

Reaction Steps

Benzyl bromide (0.45 ml, 3.8 mmol) was added to a solution of (E)-3-fluoro-4-(2-phenylethenyl)pyridine (0.6781 g, 3.40 mmol) in anhydrous dimethylformamide (5 ml) and the mixture stirred at 90° C. under nitrogen for 1 hour. The mixture was allowed to cool and diluted with ethanol (50 ml). Sodium borohydride (0.1580 g, 4.18 mmol) was added portionwise and the resulting reaction mixture stirred at room temperature for 2 hours. The mixture was concentrated in vacuo, water (100 ml) added and extracted with diethyl ether (2×100 ml). The extracts were washed with brine (100 ml), combined, dried (MgSO4) and concentrated in vacuo. Careful purification by first flash chromatography, eluting with ethyl acetate/petrol (60°-80°), followed by preparative layer chromatography, eluting with ethyl acetate/dichloromethane/petrol (60°-80°), gave the title compound (0.1058 g, 11%) as a pale yellow solid; δH (CDCl3) 2.43 (2H, m, tetrahydropyridinyl CH2), 2.69 (2H, m, tetrahydropyridinyl CH2), 3.18 (2H, br s, tetrahydropyridinyl CH2), 3.67 (2H, s, PhCH2N), 6.42 (1H, d, J 16.4Hz, CH=CHPh) and 7.20-7.49 (11H, m, CH=CHPh and ArH).

Provenance & Evidence