Thionyl Chloride → 1-benzyl-3-(chloromethyl)-5-methoxy-1H-indazole

Participants

Reaction Steps

To a solution of (1-benzyl-5-methoxy-1H-indazol-3-yl)methanol (18 g; 0.07 mol) in chloroform (200 ml) stirred at room temperature was slowly added thionyl chloride (15.8 g; 0.13 mol). Once the addition was complete, the solution was refluxed for 24 hours. The reaction was then stopped by cooling the mixture to room temperature and evaporating off the solvent under reduced pressure. The residue was then taken up several times in toluene and concentrated under reduced pressure. The crude residue obtained was purified by crystallization from hexane to give 9.5 g of 1-benzyl-3-(chloromethyl)-5-methoxy-1H-indazole with a melting point of 78-80° C.

Provenance & Evidence