1,2-Dibromoethane → 4-(2-Bromoethoxy)-3-fluorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-fluoro-4-hydroxybenzonitrile (1.2 g, 8.76 mmol), anhydrous K2CO3 (2.43 g, 17.6 mmol) and 1,2-dibromoethane (4.5 mL, 52.0 mmol) in DMF (6 mL) was stirred at 60° C. overnight under a nitrogen atmosphere. The reaction mixture was filtered and the filtrate was extracted with ethyl acetate. The extract was washed with water and brine, dried over sodium sulfate. Solvent evaporation under reduced pressure, followed by column chromatography over silica gel (eluent: petroleum ether/ethyl acetate=5/1), gave 1.52 g (71%) of the subtitle compound as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.43 (d, J=9.2 Hz, 1H), 7.40 (d, J=12.0 Hz, 1H), 7.03 (dd, J=8.0 Hz, 8.4 Hz, 1H), 4.42 (t, J=6.2 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H).

Provenance & Evidence