3-Fluorobenzyl bromide → 5-[(3-Fluorobenzyl)sulfanyl]-2,3-bis(methoxymethoxy)pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-{[5,6-bis(methoxymethoxy)pyridin-3-yl]sulfanyl}propanoate (Intermediate 42; 1 g, 3.15 mmol) in THF (17 ml) at −45° C. was added potassium ten-butoxide (0.389 g, 3.47 mmol). After stirring at −45° C. temperature for 1 hour, 1-(bromomethyl)-3-fluorobenzene (0.715 g, 3.78 mmol) was added and the reaction mixture stirred for 3 hours. Upon warming to room temperature the reaction mixture was partitioned between dichloromethane and water. The aqueous phase was re-extracted and the combined organic extracts were washed with brine, dried and concentrated in vacuo. The crude product was purified by column chromatography (SiO2; 0-50% ethyl acetate/petrol) to yield 5-[(3-fluorobenzyl)sulfanyl]-2,3-bis(methoxymethoxy)pyridine (690 mg, 64%).

Provenance & Evidence