Sodium hydride → Tert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylate

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The mixture of 1-bromo-3-(bromomethyl)benzene (6.2 g, 24.8 mmol) and triethyl phosphite (4.53 g, 27.28 mmol) was heated at 90° C. for 12 hours, cooled to 0° C., added DME (40 ml) and tert-butyl 4-oxopiperidine-1-carboxylate (5.73 g, 28.8 mmol) and sodium hydride (1.19 g, 49.6 mmol) and stirred at RT for 2-3 hours. Diluted with water and extracted with ether to afford 4.5 g (51.5% yield) of the titled product after purification with (60/120 silica gel) column chromatography using 10% ethyl acetate in hexane as eluent. MS: m/z=353.2 (M+1).

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