Chloromethyl Methyl Ether → 4-Chloromethylbenzocyclobutene

Participants

Reaction Steps

To a stirred solution of 10 g of benzocyclobutene and 18.25 mL of chloromethyl methyl ether in 100 mL of methylene chloride at -78° C. under a nitrogen atmosphere, 11.1 g tin tetrachloride was added slowly over a period 1 hour and stirring was continued for 6 more hours at -78° C. The reaction mixture was then poured into an ice cold sodium hydroxide solution (10%) and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. Removal of the solvent followed by purification by flash chromatography afforded 6 g of 4-chloromethylbenzocyclobutene (41%) as a colorless liquid.

Provenance & Evidence