4-bromo-2-butoxybenzonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-bromo-2-hydroxy-benzonitrile (0.89 g, 4.45 mmol) in THF (50 mL) and 1-butanol (2.0 mL) is slowly added to NaH (0.356 g, 8.90 mmol). The mixture is stirred at room temperature for one hour and quenched with water (10 mL). The mixture is concentrated, and the residue is extracted with ethyl acetate (20 mL×2). The combined organic layers are dried over sodium sulfate and concentrated to provide 4-bromo-2-butoxy-benzonitrile (0.65 g, 57%). 1H NMR (400 MHz, CDCl3): δ 7.37-7.34 (d, 1H), 7.11-7.08 (d, 1H), 7.08 (s, 1H), 4.04-4.01 (t, 2H), 1.80 (tt, 2H), 1.50 (tt, 2H), 0.95 (t, 3H). quenched with water (10 mL) The mixture is concentrated the residue is extracted with ethyl acetate (20 mL×2) The combined organic layers are dried over sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-bromo-2-hydroxy-benzonitrile (0.89 g, 4.45 mmol) in THF (50 mL) and 1-butanol (2.0 mL) is slowly added to NaH (0.356 g, 8.90 mmol). The mixture is stirred at room temperature for one hour and quenched with water (10 mL). The mixture is concentrated, and the residue is extracted with ethyl acetate (20 mL×2). The combined organic layers are dried over sodium sulfate and concentrated to provide 4-bromo-2-butoxy-benzonitrile (0.65 g, 57%). 1H NMR (400 MHz, CDCl3): δ 7.37-7.34 (d, 1H), 7.11-7.08 (d, 1H), 7.08 (s, 1H), 4.04-4.01 (t, 2H), 1.80 (tt, 2H), 1.50 (tt, 2H), 0.95 (t, 3H). quenched with water (10 mL) The mixture is concentrated the residue is extracted with ethyl acetate (20 mL×2) The combined organic layers are dried over sodium sulfate concentrated