Water → 3-(5-Bromo-2-methyl-thiophen-3-yl)-propionitrile

Participants

Reaction Steps

A solution of 3-(2-methylthiophen-3-yl)-propionitrile 60 (320 mg, 2.1 mmol) in acetic acid (5 mL) was treated with bromine (0.12 mL, 2.3 mmol) and the mixture stirred at rt for 1 hour. Water was added and the mixture was extracted with EtOAc (2×20 mL). The combined organics were washed with water and dried over MgSO4. Removal of the solvent followed with silica gel column chromatography (eluent: DCM/hexane, 1/1) gave 61 as a colorless liquid (330 mg). 1H NMR (400 MHz, CDCl3) δ: 2.35 (s, 3H), 2.53 (t, J=10.5 Hz, 2H), 2.84 (t, J=10.5 Hz, 2H) 6.80 (s, 1H).

Provenance & Evidence