2-ethoxy-4-iodo-N,N-dimethylaniline

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N-dimethyl-2-ethoxy-4-iodo-aniline (0.75 g, 2.58 mmol) was dissolved in DMF (4 mL). Zinc cyanide (0.18 g, 1.54 mmol) was added. Argon was passed through the mixture for 10 min. Tetrakis(triphenylphosphine)palladium (148 mg, 0.13 mmol) was added and the mixture was heated at 110° C. for 24 h. The reaction mixture was cooled and poured into water. The mixture was extracted with ethyl acetate, washed with brine and dried over magnesium sulfate. Evaporation of the solvents and chromatography of the residue over silica gel using 20% ethyl acetate in hexanes gave N,N-dimethyl-2-ethoxy-4-cyano-aniline (187 mg, 38%). The reaction mixture was cooled The mixture was extracted with ethyl acetate washed with brine dried over magnesium sulfate Evaporation of the solvents and chromatography of the residue over silica gel using 20% ethyl acetate in hexanes