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General Procedure for Synthesis of 2-hydroxy-N-
trifluoroacetanilides from N-vinylaniline and N-allylaniline: In a
typical procedure, N-vinylaniline (0.1g, 0.840 mmol) was
dissolved in dry dioxane under inert atmosphere. To this was
added trifluoroaceticacid (0.26 ml, 3.36 mmol) and oxone (0.515g,
1.68 mmol). The resulting mixture was heated to 90 oC under
nitrogen atmosphere until starting material is consumed. During
the progress of reaction, color of reaction mixture turned from
light red to dark red. The mixture was then cooled to room
temperature, washed with saturated solution of sodium
bicarbonate. The mixture was extracted with EtOAc (20 mLx2).
The combined organic layer was dried over Na2SO4. After
removal of the solvent under reduced pressure in vaccuo, the
obtained residue was purified on silica-gel (100-200 mesh)
column chromatography (Hexane: EtOAc = 9:1) to afford a light
brown solid (60%) 2-hydroxy-N-trifluoroacetanilides, 3a. 1H
NMR (400 MHz, MeOD): δ 7.58 (d, J = 8.0 Hz, 1H), 7.00 (t, J =
7.8 Hz, 1H), 6.84 – 6.70 (m, 2H); 13C NMR (101 MHz, MeOD): δ
150.68, 128.45 , 124.75 , 124.36 , 120.61, 118.97 , 116.58 ,
116.11; 19F NMR (376.50 MHz, MeOD): δ -77.14 (s, 3F);
-1
IR(CHCl3) λmax(cm ): 3389, 3248, 2923, 2851, 1690, 1597, 1562,
1465, 1194, 1159, 1101,1041, 851, 749 ; HRMS (ESI) calcd for
C8H5F3NO2 ([M-H+]- ) 204.0275, found 204.0273; Light brown
solid; Mp: 155-156 oC.