Benzene, 1-bromo-3-nitro- → Tert-butyl 4-(2-bromo-4-nitrophenoxy)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of 1-t-butoxycarbonyl-4-hydroxypiperidine (2.7 g), 3-bromo-4-hydroxynitrobenzene (1.9 g) [which was prepared from 3-bromonitrobenzene according to the method described in J. Org. Chem., 63 4199 (1998)] and triphenylphosphine (4.4 g) in dichloromethane (50 ml) was added dropwise diethyl azodicarboxylate (2.7 ml) and the mixture was stirred at room temperature for 11.5 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=2/1 as an eluant to give the desired compound (3.1 g, yield 91%) as a yellow oil.

Provenance & Evidence