Sulfuryl chloride → HCID 14348768, compound

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Reaction Steps

A portion (10 g) of the 7,8-dihydro-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-methanol prepared in Example 1 was dissolved in 300 ml of methylene chloride. To the ice-cooled solution, sulfuryl chloride (9 g) was added over time under agitation. The mixture was thereafter stirred for 8 hours at room temperature. The solvent was distilled off and the resulting residue was purified by column chromatography using methylene chloride as an eluant, whereupon 3.3 g of 5-chloro-7,8-dihydro-3-phenylfuro[2,3-g]-1,2benzisoxazole-7-methanol was obtained. This compound (3.3 g) was dissolved in 100 ml of acetone and, to the stirred solution, a mixture of chromium (VI) oxide (4 g), water (6 ml) and concentrated sulfuric acid (5.9 g) was added dropwise over time, and the solution was stirred for 2.5 hours at room temperature. The insolubles were filtered off by suction. After distilling off the acetone, water was added to the residue and the mixture was subjected to extraction with ether. The ether layer was washed with water and dried, followed by distilling off of the solvent. The residue was recrystallized with acetonitrile to yield 1 g of 5-chloro-7,8-dihydro-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acid. m.p. 221°-224° C. This compound exhibited a mass spectrum having a molecular ion peak at m/e 315.

Provenance & Evidence