Carbon Dioxide → HCID 70298268, compound

Participants

Reaction Steps

A stirred solution of 6-fluoro-3-methyl-1,2(2H)-benzisoxazole (5.5 g, 0.037 mole) in THF (100 mL) was cooled in a dry ice-acetone bath, and 2.5 M n-butyllithium in hexanes (16 mL, 0.040 mole) was added dropwise. Upon completion of addition, the reaction mixture was stirred for one hour. The reaction mixture was then exposed to a CO2 atmosphere where it stirred for three hours. After this time, the reaction mixture was poured into water. The mixture was washed with ether, acidified with hydrochloric acid, and then extracted repeatedly with ether. The combine extracts were washed with water, dried with magnesium sulfate and concentrated yielding 4.5 grams of [6-fluoro-3-methyl-1,2(2H)-benzisoxazol-7-yl]carboxylic acid. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence