Dichloromethane → 7-Chloro-2,2,4,5-tetramethyl-2,3-dihydro-1-benzofuran

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Reaction Steps

To a solution of 23.8 g of the methally 2-chloro-4,5-dimethylphenyl ether in 200 ml absolute dichloromethane at -70° C. was added 10 g of AlCl3 under a current of nitrogen gas. After stirring and warming to the room temperature over a period of 1 hour, the reaction mixture was added 200 ml of ice-water and the aqueous layer was extracted with dichloromethane. The organic extract was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a crude product. Final purification was carried by silica-gel column chromatography to afford 20 g of 7-chloro-2,3-dihydro-2,2,4,5-tetramethylbenzofuran as yellow oil.

Provenance & Evidence