Dodecane → N-(3,5-dimethylphenyl)-N-methylformamide

Participants

Reaction Conditions

Reaction Steps

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), K3PO4 (430 mg, 2.03 mmol), evacuated, backfilled with Ar. Hexamethylphosphorous triamide (18.5 μL, 0.102 mmol, 10 mol %) 5-iodo-m-xylene (145 μL, 1.00 mmol), N-methylformamide (72 μL, 1.23 mmol), and toluene (1.0 mL) were added under Ar. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 110° C. for 24 h. The suspension was allowed to reach room temperature. Dodecane (internal GC standard, 230 μL) and ethyl acetate (2 mL) were added. A 0.1 mL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC to provide 76% yield of N-(3,5-dimethylphenyl)-N-methylformamide.

Provenance & Evidence