Water → HCID 17989205, compound

Participants

Reaction Conditions

Reaction Steps

17.6 g (100.8 mmol) of 2-chloro-6-fluoro-3-methylanisole is dissolved in 880 ml of toluene. After 27.8 g (403.2 mmol) of isobutyric acid nitrile is added, 302.4 ml (151.2 mmol) of a 0.5 molar solution of potassium hexamethyl disilazide in toluene is added in drops within 40 minutes (temperature increase to 27° C.). After 19 days of stirring at room temperature, the batch is mixed with 300 ml of water and 400 ml of ethyl acetate and then acidified with 10% sulfuric acid to a pH of 4. The aqueous phase is shaken with 200 ml of ethyl acetate. The combined organic extracts are washed with water and twice with saturated NaCl solution and then dried. After spinning-in and chromatography on silica gel (mobile solvent: ethyl acetate/hexane), 12.01 g (53.4%) of the desired compound is obtained.

Provenance & Evidence