Thionyl Chloride → 2-(3-Chloromethylphenoxy)methylquinoline

Participants

Reaction Steps

25.6g (93.5 mmoles) of 2-(3-hydroxymethylphenoxy)methylquinoline is dissolved in 30 ml of methylene chloride and 3 drops of dimethylformamide is added. 60.7 ml of a 2.0M solution of thionyl chloride in methylene chloride is then added dropwise at 0° C. The mixture is allowed to warm to room temperature and stirred for 5 hours. The solution is washed with sodium bicarbonate solution, dried, concentrated in vacuo and the crude product purified by silica gel HPLC to yield 12.1 g 3-(2-quinolinylmethyloxy)benzylchloride as a pale yellow solid.

Provenance & Evidence