Hydrochloric Acid → HCID 66999437, compound

Participants

Reaction Conditions

Reaction Steps

The aniline 117b (3.98 g, 10.10 mmol) was dissolved in anhydrous CH3CN (35 mL) under nitrogen. This solution was then added dropwise to a mixture of tert-butylnitrite (2.40 mL, 20.20 mmol) and CuCl2 (2.72 g, 20.20 mmol) that had been prepared under nitrogen and warmed to 60° C. The reaction temperature was maintained at 60° C. for 2 h, then cooled to 0° C. A 5% aqueous HCl solution (80 mL) was added, and the mixture was extracted with 1:1 EtOAc/hexanes (3×75 mL). The combined organics were washed with brine (75 mL), dried over anhydrous MgSO4, and evaporated. The remaining oil was purified by flash chromatography on silica gel (0% to 30% EtOAc/Hexanes) to provide 2.67 g (64%) of the [4-chloro-3-(3-bromo-5-cyano-phenoxy)-2-fluoro-phenyl]-acetic acid ethyl ester (117c).

Provenance & Evidence