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136.3, 130.6, 130.3, 129.3, 128.5, 128.3, 128.0, 127.1, 127.0, 125.8, 747, 615. MS (ESI): m/z 309 (M + H)+. HRMS (ESI): m/z calcd for
125.5, 113.4, 103.7, 98.6, 55.6, 55.2, 55.2, 48.3 ppm. IR (lm, C20H18ClO [M + H]+ 309.1041, found 309.1050.
cmꢁ1): 2802, 1664, 1596, 1327, 932, 815, 804, 730, 623. MS (ESI):
((4-(Triuoromethyl)phenyl)methylene)dibenzene
m/z 335 (M + H)+. HRMS (ESI): m/z calcd for C22H23O3 (M + H)+ Prepared following the general procedure A. Rf: 0.5 (1% EtOAc
335.1642, found 335.1632.
in Hex). Yield: 56%. 1H NMR (400 MHz, CDCl3): d 7.54–7.52 (m,
1,3-Dimethoxy-2-((4-methoxyphenyl)(o-tolyl)methyl)benzene 2H), 7.31–7.21 (m, 8H), 7.10–7.08 (m, 4H), 5.59 (s, 1H) ppm. 13
(3cj).
C
(3ae). Prepared following the general procedure A. Rf: 0.3 (4% NMR (100 MHz, CDCl3): 148.0, 142.9 (2C), 129.7, 129.3 (6C),
1
EtOAc in Hex). Yield: 72%, H NMR (400 MHz, CDCl3): d 7.17– 128.5 (6C), 126.6, 125.2, 125.2, 56.6. IR (lm, cmꢁ1): 2812, 1664,
6.28 (m, 11H), 5.76 (s, 1H), 3.70 (s, 6H), 3.60 (s, 3H), 2.10 (s, 1543, 1320, 932, 815. MS (ESI): m/z 313 (M + H)+. HRMS (ESI): m/
3H) ppm. 13C NMR (100 MHz, CDCl3): 159.3, 157.9, 157.7, 143.0, z calcd for C20H16F3 [M + H]+ 313.1199, found 313.1198.
136.6, 135.6, 130.5, 130.3, 130.1 (2C), 128.7 (2C), 125.9, 125.4,
4-((2-Fluoro-5-nitrophenyl)(phenyl)methyl)-1,10-biphenyl (3dk).
125.0, 113.4, 103.7, 98.6, 55.6, 55.2, 55.1, 45.1, 19.5 ppm. IR Prepared following the general procedure B. Rf: 0.5 (3% EtOAc in
(lm, cmꢁ1): 2902, 1685, 1536, 1347, 911, 776. MS (ESI): m/z 349 Hex). Yield: 42%, 1H NMR (400 MHz, CDCl3): d 7.58–7.54 (m, 4H),
(M + H)+. HRMS (ESI): m/z calcd for C23H25O3 (M + H)+ 349.1798, 7.45–7.32 (m, 6H), 7.29–7.25 (m, 7H), 5.48 (s, 1H) ppm. 13C NMR
found 349.1810.
(100 MHz, CDCl3): 145.2, 142.1, 140.8, 140.0, 137.8, 132.3, 130.7,
1-((4-Ethoxyphenyl)(phenyl)methyl)-2-methoxybenzene (3bg). 130.0, 128.9, 128.7, 128.4, 128.3 (4C), 128.1 (2C), 127.6 (2C), 127.3,
Prepared following the general procedure A. Rf: 0.3 (2% EtOAc in 127.2, 127.1, 127.0, 126.9, 79.8. IR (lm, cmꢁ1): 2883, 1904, 1684,
Hex). Yield: 68%, 1H NMR (400 MHz, CDCl3): d 7.08–6.29 (m, 13H), 1892, 1543, 871, 810, 742, 613. MS (ESI): m/z 384 (M + H)+. HRMS
5.62 (s, 1H), 3.90 (m, 2H), 3.62 (s, 3H), 1.31 (t, 3H, J ¼ 5.4 Hz) ppm. (ESI): m/z calcd for C25H19FNO2 [M + H]+ 384.1394, found
13C NMR (100 MHz, CDCl3): 157.0, 156.2, 144.6, 136.2, 136.1, 132.6, 384.1402.
132.5, 130.0 (2C), 129.1 (3C), 127.9 (2C), 125.6, 124.3, 113.9, 95.5,
2-((4-Methoxyphenyl)(o-tolyl)methyl)-1,3-dimethylbenzene (3ef).
63.3, 55.8, 48.2, 14.9 ppm. IR (lm, cmꢁ1): 2815, 1664, 1592, 1585, Prepared following the general procedure A. Rf: 0.5 (2% EtOAc
1320, 1104, 932, 812, 730, 623. MS (ESI): m/z 319 (M + H)+. HRMS in Hex). Yield: 74%. 1H NMR (400 MHz, CDCl3): d 7.42–7.40 (m,
(ESI): m/z calcd for C22H23O2 [M + H]+ 319.1693, found 319.1693.
1H), 7.31–7.12 (m, 10H), 5.40 (s, 1H), 3.38 (s, 3H), 2.26 (s,
2-((3,4-Dimethoxyphenyl)(phenyl)methyl)-1,3-dimethoxyben- 9H) ppm. 13C NMR (100 MHz, CDCl3): 144.6, 141.8, 141.4,
zene (3ah). Prepared following the general procedure A. Rf: 0.3 141.0, 139.9, 139.6, 136.4, 136.0, 130.6, 130.5, 128.3, 128.2,
(5% EtOAc in Hex). Yield: 79%, 1H NMR (400 MHz, CDCl3): 127.9, 127.6, 127.4, 126.2, 126.1 (2C), 57.1, 47.4, 19.5 (2C),
d 7.18–6.29 (m, 11H), 5.68 (s, 1H), 3.76 (s, 3H), 3.70 (s, 3H), 3.67 19.3 ppm. IR (lm, cmꢁ1): 2984, 1683, 1317, 981, 823, 728, 604.
(s, 3H), 3.61 (s, 3H) ppm. 13C NMR (100 MHz, CDCl3): 158.2, HRMS (ESI): m/z calcd for C23H25O [M + H]+ 317.1900, found
156.8, 147.4, 146.0, 143.3, 135.6, 129.4 (2C), 128.1 (2C), 126.8, 317.1898.
124.7, 124.2, 120.1, 111.7, 109.5, 102.6, 97.5, 54.6, 54.6, 54.4,
4-((2-Nitrophenyl)(phenyl)methyl)-1,10-biphenyl
(3).
54.1, 47.5 ppm. IR (lm, cmꢁ1): 2805, 1664, 1587, 1523, 1320, Prepared following the general procedure A. Rf: 0.4 (2% EtOAc
1104, 897, 816. MS (ESI): m/z 365 (M + H)+, HRMS (ESI): m/z calcd in Hex). Yield: 49%, 1H NMR (400 MHz, CDCl3): d 7.58–7.54 (m,
for C23H25O3 [M + H]+ 365.1747, found 365.1756.
5H), 7.46–7.40 (m, 7H), 7.36–7.28 (m, 6H), 5.48 (s, 1H) ppm. IR
((2-Methoxyphenyl)methylene)dibenzene (3ba). Prepared (lm, cmꢁ1): 2873, 1796, 1676, 1579, 1544, 923, 815, 794, 745,
following the general procedure A. Rf: 0.5 (1% EtOAc in Hex). 631. HRMS (ESI): m/z calcd for C25H20NO2 [M + H]+ 366.1489,
1
Yield: 71%, H NMR (400 MHz, CDCl3): d 7.27–6.79 (m, 14H), found 366.1499.
5.48 (s, 1H), 3.75 (s, 3H) ppm. 13C NMR (100 MHz, CDCl3): 158.0,
1-((4-Methoxyphenyl)(3-(triuoromethyl)phenyl)methyl)-3-
144.3 (2C), 136.1, 130.4 (2C), 129.4 (5C), 128.3 (4C), 126.2 9 (2C), nitrobenzene (3gl). Prepared following the general procedure B.
113.7, 56.0, 55.2 ppm. IR (lm, cmꢁ1): 2943, 1685, 1576, 1280, Rf: 0.4 (3% EtOAc in Hex). Yield: 51%. 1H NMR (400 MHz,
810, 730. MS (ESI): m/z 275 (M + H)+. HRMS (ESI): m/z calcd for CDCl3): d 7.85–7.79 (m, 1H), 7.56–7.51 (m, 2H), 7.42–7.36 (m,
C20H19O [M + H]+ 275.1430, found 275.1439.
3H), 7.09–7.06 (m, 2H), 7.01–7.00 (m, 2H), 6.85–6.82 (m, 2H),
Triphenylmethane (3ca). Prepared following the general 5.85 (s, 1H), 3.80 (S, 3H) ppm. IR (lm, cmꢁ1): 2907, 1886, 1673,
1
procedure A. Rf: 0.5 (1% EtOAc in Hex). Yield: 67%, H NMR 1584, 1543, 1281, 942, 881, 634. HRMS (ESI): m/z calcd for
(400 MHz, CDCl3): d 7.33–7.09 (m, 15H), 5.54 (s, 1H) ppm. 13C
C
21H17F3NO3 [M + H]+ 388.1155, found 388.1149.
NMR (100 MHz, CDCl3): 143.9 (3C), 129.5, 128.3 (6C), 128.3 (6C),
1-Chloro-3-((4-methoxyphenyl)(3-(triuoromethyl)phenyl)-
128.2, 126.3, 56.9 ppm. IR (lm, cmꢁ1): 2987, 1642, 1586, 1572, methyl)benzene (3hl). Prepared following the general procedure
1121. MS (ESI): m/z 245 (M + H)+. HRMS (ESI): m/z calcd for B. Rf: 0.2 (2% EtOAc in Hex). Yield: 56%. H NMR (400 MHz,
1
C
19H17O [M + H]+ 245.1325, found 245.1329.
CDCl3): d 7.24–7.22 (m, 1H), 7.04–6.98 (m, 2H), 6.95–6.93 (m,
1-((4-Chlorophenyl)(phenyl)methyl)-2-methoxybenzene (3bi). 3H), 6.89–6.88 (m, 2H), 6.85–6.84 (m, 1H), 6.82–6.79 (m, 2H),
Prepared following the general procedure A. Rf: 0.3 (2% EtOAc in 6.63–6.62 (m, 1H), 5.82 (s, 1H), 3.78 (S, 3H) ppm. IR (lm, cmꢁ1):
Hex). Yield: 62%. 1H NMR (400 MHz, CDCl3): d 7.25–7.19 (m, 6H), 2928, 1691, 1564, 1298, 911, 828, 804. HRMS (ESI): m/z calcd for
7.07–6.99 (m, 4H), 6.87–6.79 (m, 3H), 5.87 (s, 1H), 3.69 (s,
C
21H17ClF3O [M + H]+ 377.0915, found 377.0919.
2-Benzhydrylthiophene (5). Prepared following the general
3H) ppm. 13C NMR (100 MHz, CDCl3): 157.0, 143.3, 142.5, 132.1,
1
131.8, 130.7, 130.2, 129.4 (2C), 128.2 (5C), 127.8, 126.2, 120.3, procedure A. Rf: 0.6 (1% EtOAc in Hex). Yield: 50%. H NMR
110.7, 55.5, 49.0 ppm. IR (lm, cmꢁ1): 2763, 1675, 1297, 981, 824, (400 MHz, CDCl3): d 7.30–7.17 (m, 11H), 6.92 (m, 1H), 6.68 (m,
1H), 5.67 (s, 1H) ppm. 13C NMR (100 MHz, CDCl3): 147.9, 143.8
6970 | RSC Adv., 2017, 7, 6966–6971
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