N-Methylaniline → N-Methyl-N-(2,2,2-trifluoroethyl)aniline

Participants

Reaction Conditions

Reaction Steps

Fluorinated light-absorbing electron donors were prepared. N-Methyl-N-2,2,2-trifluoroethylaniline was prepared as follows. Into a flask were placed N-methylaniline (6.0 g) and potassium carbonate (10.0 g) the flask was assembled with a refluxing condenser. To the flask was slowly added 2,2,2-trifluoroethyl trifluoromethanesulfonate (13 g). After addition, the reaction mixture was stirred and heated to 100-110° C. overnight. The reaction mixture was then quenched by addition of 100 mL of water. The water solution was extracted with diethyl ether (2×50 mL). The organic layer was separated and dried over MgSO4. Ether was removed under vacuum. The organic liquid was distilled to receive a fraction (a clear yellow liquid, 9.2 g) at 44-45° C. (at 0.05 mm Hg). The clear liquid was sampled and analyzed by 1H and 19F NMR. 1H NMR: δ7.28 (t, 2H, J=8 Hz), 6.81 (m, 3H), 3.83 (q, 2H, J=9H), 3.04 (s, 3H); 19F NMR: δ−73.37 (t, 3F. J=9 Hz).

Provenance & Evidence