Ethanone, 2,2,2-trifluoro-1-[2-(methylamino)phenyl]- (9CI) synthesis

Yield:202270-41-5 61%

Reaction Conditions:

with tetrabutyl ammonium fluoride in tetrahydrofuran at 0 - 20; for 20 h;Inert atmosphere;

Steps:

4.2.5. Synthesis of 2,2,2-trifluoro-1-[2-(methylamino)phenyl]ethanone (2a) by the reaction in THF

To a solution of 1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione 1a (0.61 g, 3.45 mmol) and trimethyl(trifluoromethyl)silane (638 mg, 4.49 mmol) in dry THF (15 ml) was added TBAF (1M in THF; 0.52 ml, 0.52 mmol) dropwise at 0 8C under argon. After completion of addition, the reaction mixture was allowed to warm to rt and stirred for 24 h. The reaction was quenched with 5% aq HCl solution (10 ml) at 0 8C, allowed to warm to rt, and stirred 0.5 h.To the reaction mixture was added 10% aq Na2CO3 solution (50 ml) under vigorous stirring, and stirring was continued for 1 h at rt. The resulting solution was extracted with hexanes (60 ml 3). The organic layer was washed with brine (30 ml 2), dried over anhydrous MgSO4, and concentrated under reduced pressure

References:

Shidlovskii, Alexander F.;Golubev, Alexander S.;Gusev, Dmitrii V.;Suponitsky, Kyrill Yu.;Peregudov, Alexander S.;Chkanikov, Nikolai D. [Journal of Fluorine Chemistry,2012,vol. 143,p. 272 - 280,9]