HCID 68430396, compound → HCID 68534886, compound

Participants

Reaction Conditions

Reaction Steps

3-(4-Iodomethyl-phenoxy)-benzonitrile is prepared by an analogous procedure described in Preparation 43. Add half of a solution of 3-(4-iodomethyl-phenoxy)-benzonitrile (470 mg, 1.4 mmol) in anhydrous dimethylformamide (10 mL) to 1-(2,4-dihydroxy-3-trifluoromethyl-phenyl)-ethanone (300 mg, 1.4 mmol) and Li2CO3 (228 mg, 3.1 mmol) in anhydrous dimethylformamide (18 mL)dimethylformamide. Heat the reaction mixture to 60° C. and stir for 1 h. Add the other half of the 3-(4-iodomethyl-phenoxy)-benzonitrile solution to the reaction mixture. Stirred at 60° C. for an additional 1 h, cool to room temperature, and quench with water (75 mL). Extract the aqueous mixture with ethyl acetate (3×75 mL). Combine the organic layers, wash with brine, dry over sodium sulfatesodium sulfate, and concentrate. Purify the residue by flash column chromatography using 50% ethyl acetate/hexane as the eluent to give the title compound (302 mg, 50%). LC-MS (m/e): 426 (M−1)

Provenance & Evidence