Benzyl Chloride → 1,3-Dibenzyl-5-bromo-1H-pyridin-4-one

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Reaction Steps

A mixture of 3-benzyl-5-bromopyridin-4-one 12 (0.57 g, 2.16 mmol) and NaOEt (0.89 mL, 2.37 mmol) in absolute ethanol (20 mL) was refluxed with benzyl chloride (0.30 mL, 2.59 mmol) for 1 h under nitrogen. The solvent was distilled off to give a yellow residue which was purified by flash column chromatography on silica gel (dichloromethane:methanol, 98:2). Yield 1.31 g (96.7%), yellow solid, mp 120-121° C. 1H NMR (CDCl3, 500 MHz): δ 7.67 (d, 1H, J=2.4), 7.32-7.07 (m, 10H), 4.83 (s, 1H), 3.78 (s, 2H). 13C NMR (CDCl3, 125 MHz): δ 172.2, 139.6, 139.1, 137.6, 134.7, 129.9, 129.9, 129.3, 129.3, 129.2, 129.0, 128.6, 128.6, 127.5, 127.6, 126.4, 114.1, 60.3, 34.4. HRMS (M+H)+ calcd for C19H16BrNO 354.0494, found 354.0499.

Provenance & Evidence