Dimethylformamide → 5-(4-Fluorophenoxy)-2-thiophenecarboxaldehyde

Participants

Reaction Steps

To a solution of 2-(4-fluorophenoxy)thiophene (3.66 g, 18.9 mmol) in THF (90 mL) at -78° C., was added butyllithium (7.5 ml of a 2.5M solution in hexanes, 18.9 mmol) dropwise. Upon completion of addition, the mixture was stirred for 20 min. N,N-Dimethylformamide (1.52 g, 20.8 mmol) was then added and the reaction was stirred for 40 min at -78° C. It was then quenched with saturated aqueous NH4Cl (100 mL) and extracted with ethyl acetate (3×100 mL). The organics were combined, dried over MgSO4 and concentrated. The resulting residue was chromatographed (silica gel; 3:1 hexanes, ether) to afford 3.59 g (86%) of 5-(4-fluorophenoxy)-2-thiophenecarboxaldehyde as a slightly orange solid.

Provenance & Evidence