Sodium Azide → HCID 86609110, compound

Participants

Reaction Steps

A solution of toluene-4-sulfonic acid 8-(2-chloro-phenyl)-6-fluoro-chroman-2-ylmethyl ester (253 mg, 0.566 mmol) and sodium azide (147 mg, 2.264 mmol) in anhydrous dimethyl sulfoxide (8 mL) was heated to 70° C. under nitrogen for 20 hours. The cooled reaction mixture was quenched by the addition of water (30 mL) and the resulting suspension stirred vigorously for 10 minutes. The mixture was then partitioned between ethyl acetate (100 mL) and water (100 mL), the organic phase separated, washed with water (100 mL) and saturated brine (100 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford 170 mg (95%) of 2-azidomethyl-8-(2-chloro-phenyl)-6-fluoro-chroman a colorless syrup.

Provenance & Evidence