2-Cyano-5-fluorobenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromo-4-fluorobenzonitrile (5.0 g, 25.0 mmol) in anhydrous THF (20 mL) is added iPrMgCl 2.01\4 in THF (15.0 mL, 30.0 mmol) at −30° C. The solution is stirred at −30° C. for 3 hours and DMF (5.80 mL, 75.0 mmol) is added. The reaction mixture is allowed to warm to room temperature and is stirred for 1 hour. The solution is cooled to −10° C., 2M hydrochloric acid (37 mL) is added and the solution is stirred for 20 minutes. The solution is concentrated in vacuo to −⅓ original volume and extracted into EtOAc (3×). The combined organics are then dried (Na2SO4), filtered and concentrated to afford 4-fluoro-2-formyl benzonitrile (3.9 g, 71%). to warm to room temperature is stirred for 1 hour The solution is cooled to −10° C. the solution is stirred for 20 minutes The solution is concentrated in vacuo to −⅓ original volume extracted into EtOAc (3×) The combined organics are then dried (Na2SO4) filtered concentrated