N,N-Dimethylaniline → HCID 23440323, compound

Participants

Reaction Steps

4-(Pentafluoroisopropyl)-N,N-dimethylaniline was prepared as follows. A flask was charged with N,N-dimethylaniline (10.2 g), perfluoroisopropyl iodide (25 g), N,N-dimethyl formamide (35 mL) and water (15 mL). To the flask was slowly added a mixture of NaS2O4 (17.5 g) and NaHCO3 (8.5 g). The reaction started immediately when the mixture of NaS2O4/NaHCO3 was introduced, thus the flask was cooled with an ice-water bath. After addition, the mixture was stirred at room temperature overnight. The mixture was poured into 200 mL water. The mixture was then extracted with diethyl ether (4×50 mL). The ether solution was dried over MgSO4. The ether was removed under reduced pressure to give a crude mixture of ortho- and para-substituted perfluoroisopropyl aniline and a bit of the starting aniline (10.0 g). The higher boiling point liquid was distilled to produce a fraction at 38-45° C. (at 0.05 mm Hg) (a mixture of para- and ortho-substituted products as a yellow liquid, 5.5 g). and a fraction at 45-48° C. (at 0.05 mm Hg) (para-substituted perfluoroisopropyl-N,N-dimethylaniline, 3.8 g). The liquid was sampled and analyzed by 1H and 19F NMR. 1H NMR: δ7.35 (d, 2H, J=8 Hz), 6.64 (d, 2H, J=8 Hz), 2.94 (s, 6H); 19F NMR: δ−75.3 (6F), −174.2 (F).

Provenance & Evidence