5-Bromo-2-fluorobenzaldehyde → 5-Cyano-2-fluorobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-bromo-2-fluorobenzaldehyde (9.2 g, 45 mmol) in DMF (5 mL) was added CuCN (4.8 g, 54 mmol) and the mixture was heated at 100° C. for 2 hours and at 130° C. overnight. The mixture was cooled to room temperature, added to a solution of FeCl2 (11 g) in conc. HCl (100 mL) and H2O (500 mL) and stirred at room temperature for 30 minutes. The aqueous was extracted with CH2Cl2 (4×200 mL) and the combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude material was purified to afford 5-cyano-2-fluorobenzaldehyde as a yellow solid (5.0 g, 75%).

Provenance & Evidence