N-bromobutanimide → HCID 18446536, compound

Participants

Reaction Steps

To a solution of 3-[2-(3-hydroxy-propyl)-thiophen-3-yl]-propionitrile 83 (0.18 g, 0.9 mmol) in DMF (2 mL) was added NBS (0.18 g, 0.99 mmol). The mixture was then stirred at room temperature for 6 hours and then concentrated in vacuo. A solution of the residue in CH2Cl2 (80 mL) was washed with water, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel column chromatography (eluent: 50% EtOAc in hexane) afforded 84 (0.08 g). 1H NMR (400 MHz, d6-DMSO) δ: 7.06 (s, 1H), 4.53 (t, J=6.0 Hz, 1H), 3.41 (dd, J=6.0 and 11.5 Hz, 2H), 2.75 (m, 6H), 1.67 (m, 2H). MS (EI) m/z [(M+H+) (79Br)] 274, [(M+H+) (81Br)] 276, [(M−OH+) (79Br)] 256 and [(M−OH+) (81Br)] 258.

Provenance & Evidence