HCID 22404751, compound → HCID 22404770, compound

Participants

Reaction Steps

One thousand mL of stirred, 1,2-dichlorobenzene was heated to 180 ° C., and a solution of 75.0 grams (0.37 mole) of 3-(2-cyano-3-fluorophenoxy)-3-methyl-1-butyne in 100 mL of 1,2-dichlorobenzene was added dropwise. Upon completion of the addition, the reaction mixture was stirred at 180° C. for one hour, after which the reaction mixture was cooled and subjected to column chromatography on silica gel. The 1,2-dichlorobenzene solvent was separated by elution with hexane. The product was removed from the column by elution with methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 37.0 of 8-cyano-2,2-dimethyl-7-fluoro-2H-1-benzopyran, mp 99°-101° C. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence