Hydrochloric Acid → HCID 76710731, compound

Participants

Reaction Steps

To an ice-cooled and stirred mixture of 2-amino-5-[4-(methylsulfonyl)phenoxy]phenol (4.3 g) and concentrated hydrochloric acid (2.8 mL) in ethanol (40 mL) and acetonitrile (10 ml) was added a solution of sodium nitrite (1.27 g) in water (5 mL) at −5 to −10° C., and the mixture was diluted with water (20 mL). After stirred at −5 to −10° C. for 30 min, the resulting clear brown solution was added dropwise to a cooled solution of potassium hydroxide (85%, 3.05 g) and ethyl 2-methyl-3-oxobutanoate (2.44 mL) in ethanol (30 mL) and water (30 ml) at −10 to −20° C. After stirred at −10 to −20° C. for 20 min, the mixture was partitioned between ethyl acetate and aqueous citric acid solution. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residual light brown solid was washed with ethyl acetate-hexane to give the title compound (5.81 g, 96%) as a light orange solid. MS 391 (MH+).

Provenance & Evidence