6-ChloroMethyl-2,3-dihydro-benzo[1,4]dioxine

39270-39-8

26309-99-9

General procedure for the synthesis of 6-(chloromethyl)-2,3-dihydrobenzo[b][1,4]dioxazine from benzodioxane-6-methanol: A mixture of (2,3-dihydrobenzo[1,4]dioxin-6-yl)methanol (10.6 g) with SOCl2 (10 mL) was stirred at room temperature for 10 min, followed by slow pouring of the reaction mixture into ice water. The organic layer was separated and the aqueous phase was extracted with dichloromethane (50 mL x 3). All organic layers were combined and washed sequentially with saturated NaHCO3 solution, water and brine, dried over Na2SO4 and concentrated to dryness under reduced pressure to afford 6-(chloromethyl)-2,3-dihydrobenzo[1,4]dioxin (12 g, 88% yield). The product did not require further purification and could be used directly in the next step of the reaction.