Sodium hydride → tert-Butyl 4-((3-bromo-5-nitrobenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate

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1-Bromo-3-(bromomethyl)-5-nitrobenzene (2.12 g, 7.21 mmol) and tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate (1.75 g, 6.0 mmol) were combined in dimethylformamide (18 mL) and cooled to 0° C. The reaction was treated with sodium hydride (288 mg, 12.0 mmol), stirred at 0° C. for 1 h, and at room temperature for 30 min. The reaction mixture was diluted with water and extracted with ethyl acetate (2×). The organic layers were pooled together, washed with brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (20% ethyl acetate/hexanes) gave 1.4 g (38%). 1H-NMR (CDCl3, 500 MHz) δ 8.20 (s, 1H), 7.88 (s, 1H), 7.50 (s, 1H), 7.33-7.38 (m, 4H), 4.37 (s, 2H), 3.75-3.78 (m, 2H), 3.43 (s, 2H), 3.00-3.04 (m, 2H), 2.20-2.22 (m, 2H), 1.82-1.87 (m, 2H), 1.42 (s, 9H). Mass spec.: 507.10 (MH)+.

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