10.1002/ejoc.201801645
European Journal of Organic Chemistry
with/without CH2Cl2 (0.5 mL) was magentacally stirred at room temperature (for TfOH) or -40°C
(for TfOH and FSO3H, see Table 2) for 1 h. Then reaction mixture was poured into the water (50
mL) and extracted with CHCl3 (2 × 40 mL). ). The combined extracts were consequently washed
with water (50 mL), saturated aqueous solution of Na2CO3 (25 mL), water (50 mL), dried with
anhydrous Na2SO4 and evaporated in vacuum. The obtained residue was subjected to column
chromatography on silica gel with eluation by hexanes-ethyl acetate mixtures to purify reaction
product 5.
1
1-(Trifluoromethyl)-1,3-diphenyl-1H-indene (5a). Yield of 54%. Yellow oil. H HMR
(CDCl3, 500 MHz) δ, ppm: 6.70 s (1Н, =СН), 7.32-7.39 m (4Harom.), 7.43-7.46 m (2Harom.), 7.49 t
(2Harom., J = 7.2 Hz), 7.59 d (3Harom., J = 7.6 Hz), 7.64 d (2Harom., J = 7.2 Hz), 7.69 d (1Harom., J =
13
7.6 Hz). C NMR (CDCl3, 125 MHz) δ, ppm: 64.0 q (J = 26.8 Hz), 121.6, 125.4, 126.5, 126.6 q
(CF3, J = 281 Hz), 127.78, 127.82, 128.0, 128.56, 128.63, 128.7, 130.0, 132.0, 134.3, 134.5, 143.5,
19
143.8, 147.3. F NMR (CDCl3, 470 MHz) δ, ppm: -67.4 s (CF3). MS (GC-MS, EI), (Irel.,%): 336
М+ (100), 267 (80), 252 (20), 239 (15), 189 (10). HRMS (MALDI): calculated for C22H16F3 [M+H]+
337.1199, found 337.1203.
1-Trifluoromethyl-5,6-dimethoxy-1-(3,4-dimethoxyphenyl)-3-phenylindene (5b). Yield of
75%. Yellow oil. 1H NMR (CDCl3, 300 MHz) δ, ppm: 3.83 s (3H, OCH3), 3.86 s (3H, OCH3), 3.91
s (3H, OCH3), 3.95 s (3H, OCH3), 6.55 s (1H), 6.83 d (2Harom., J = 8.5 Hz), 7.05-7.13 m (3Harom.),
13
7.21 s (1Harom.), 7.41-7.50 m (3Harom.), 7.60-7.62 m (2Harom.). C NMR (CDCl3, 75 MHz) δ, ppm:
55.89 (OCH3), 55.95 (OCH3), 56.2 (OCH3), 56.5 (OCH3), 63.9 q (J = 27 Hz), 106.5, 109.9, 111.5,
111.9, 120.8, 127.3, 127.8 q (CF3, J = 234 Hz), 128.0, 128.9, 129.2, 131.6, 135.0, 136.6, 136.8,
19
147.1, 148.6, 149.2, 149.3, 150.1. F NMR (CDCl3, 470 MHz) δ, ppm: -68.74 s (CF3). MS (GC-
MS, EI), m/z, (Irel., %): 456 M+ (100), 387 [M-CF3]+ (10). HRMS (MALDI): calculated for
C26H24F3O4 [M+H]+ 457.1621, found 457.1625.
3-(4-Chlorophenyl)-1-(trifluoromethyl)-1-phenyl-1H-indene (5c). Yield of 71%. Yellow
oil. 1H NMR (CDCl3, 500 MHz) δ, ppm: 6.70 s (1Н, =СН), 7.34-7.36 m (3Harom.), 7.39 t (1Harom., J
= 7.6 Hz), 7.44-7.47 m (3Harom.), 7.53 d (1Harom., J = 7.6 Hz), 7.56-7.58 m (4Harom.), 7.70 d (1Harom.
,
J = 7.6 Hz). 13C NMR (CDCl3, 125 MHz) δ, ppm: 64.1 q (J = 26.8 Hz), 121.4, 125.8, 126.7, 126.4 q
(CF3, J = 281 Hz), 127.8, 128.1, 128.6, 128.7, 128.9, 129.0, 132.3, 132.6, 134.1, 134.4, 143.1,
143.6, 146.1. 19F NMR (CDCl3, 470 MHz) δ, ppm: - 68.4 s (CF3). MS (GC-MS, EI), m/z, (Irel., %):
370 M+ (100), 301 [M-CF3]+ (95). HRMS (MALDI): calculated for C22H15ClF3 [M+H]+ 371.0801,
found 371.0804.
3-(4-Bromophenyl)-1-(trifluoromethyl)-1-phenyl-1H-indene (5d). Yield of 44%. Yellow
oil. 1H NMR (CDCl3, 500 MHz) , ppm: 6.67 s (1H, =CH), 7.32-7.33 m (3Harom.), 7.37 t (1Harom., J
= 7.4 Hz), 7.43 t (1Harom., J = 7.4 Hz), 7.48-7.55 m (5Harom.), 7.60-7.61 m (2Harom.), 7.67 d (1Harom.
,
J = 7.4 Hz). 13C NMR (CDCl3, 125 MHz) , ppm: 64.4 q (J = 27 Hz), 122.8, 123.0, 126.0, 126.6 q
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