N-bromobutanimide → 4-(5-Bromo-7-fluoro-2,3-dihydrobenzofuran-2-yl)piperidine

Participants

Reaction Steps

To a solution of 4-(7-fluoro-2,3-dihydrobenzofuran-2-yl)piperidine hydrochloride (1.18 g, 4.58 mmol) in MeOH (36.6 mL) at 0° C. was added NBS (0.815 g, 4.58 mmol) in one portion. Upon completion of addition, the reaction mixture was immediately warmed to room temperature, where it stirred for 3 hours. At the conclusion of this period, the reaction mixture was quenched with aqueous Na2H2S2O5 (5%, 5 mL). The solvent was removed under reduced pressure to yield a residue. The residue was diluted with CH2Cl2 (5 mL), washed with NaHCO3 (aq, sat, 3 mL) and brine (3 mL). The organic layer was separated, dried (Na2SO4), filtered, and concentrated to afford Compound 3E as a colorless oil (1.3 g, 95% yield). LC/MS (m/z)=301 (M+H)+.

Provenance & Evidence