8
Journal of Chemical Research 00(0)
1H), 7.51−7.47 (m, 2H), 7.45 (dd, J=8.7, 1.8Hz, 1H), 7.76−7.73 (m, 2H), 7.72 (d, J=1.1Hz, 1H), 7.53−7.48 (m,
7.44−7.41 (m, 1H), 7.41−7.37 (m, 1H). 13C NMR 2H), 7.47 (d, J=8.5Hz, 1H), 7.45−7.39 (m, 2H), 6.37 (d,
(151MHz, CDCl3): δ=154.7, 142.5, 131.4, 129.2, 128.7, J=9.5Hz, 1H). 13C NMR (126MHz, CDCl3): δ=160.3,
128.0, 127.7, 127.6, 123.3, 122.1, 116.4, 113.4. IR(KBr): 158.4, 149.4, 144.6, 142.9, 130.5, 129.3, 128.6, 128.3,
υ
max =3059, 2925, 1560, 1491, 1447, 1327, 1292, 1268, 124.5, 123.1, 115.3, 114.4, 114.0, 109.2. IR(KBr):
1249, 1217, 1143, 1108, 1098, 1052, 1028, 965, 866, 798, max =3150, 3052, 1740, 1629, 1594, 1543, 1497, 1487,
783, 759, 741, 712, 695, 648, and 539cm−1. MS (ESI): 1449, 1414, 1366, 1317, 1286, 1249, 1213, 1155, 1101,
υ
m/z=273.11, (100) (M+H)+.
1072, 1045, 999, 966, 927, 888, 793, 753, 722, 695, 632,
3,7-Diphenylbenzo[1,2-b:4,5-b']difuran (2l): White 612, and 523cm−1. MS (ESI): m/z=285.04, (100)
solid, m.p. 170°C–172°C (PE/Acetone, 4:1, v/v). 1H NMR [M+Na]+. HRMS (ESI): m/z (M+H)+ calcd for
+
(600MHz, CDCl3): δ=7.64 (s, 2H), 7.56 (s, 2H), 7.10−7.05 C17H13O3 : 265.07918; found: 265.07675.
(m, 4H), 6.99−6.95 (m, 2H), 6.87 (t, J=7.6Hz, 4H). 13C
3-Phenylbenzo[b]thiophene (2q): Colorless oil. The
NMR (151MHz, CDCl3): δ=153.1, 142.8, 132.9, 128.5, NMR spectra are in good agreement with the literature.70
127.7, 127.1, 124.0, 119.7, 108.8. IR(KBr): υmax =3128, 1H NMR (600MHz, CDCl3): δ=7.98−7.93 (m, 2H), 7.63
3027, 1605, 1557, 1488, 1446, 1416, 1358, 1261, 1228, (t, J=1.6Hz, 1H), 7.61 (t, J=1.5Hz, 1H), 7.54−7.50 (m,
1204, 1151, 1127, 1109, 1072, 1033, 1016, 929, 843, 807, 2H), 7.46−7.40 (m, 4H). 13C NMR (151MHz, CDCl3):
787, 753, 725, 696, 678, 601, 592, 569, and 493cm−1. MS δ=140.8, 138.2, 138.1, 136.2, 128.9(2C), 127.7, 124.6,
(ESI): m/z=311.21, (100) [M+H]+. HRMS (ESI): m/z 124.5, 123.5, 123.1(2C). IR(KBr): υmax =3057, 3027, 1483,
(M+H)+ calcd for C22H15O2 : 311.10666; found: 1425, 1347, 833, 762, 731, 697, 636, 573, and 511cm−1.
+
311.10660.
3-Phenylnaphtho[1,2-b]furan (2m): White solid, m.p.
MS (ESI): m/z=211.06, (100) (M+H)+.
3-(o-Tolyl)benzofuran (2ab): Pale yellow liquid. The
108°C–110°C (Lit67 111°C–113°C) (PE/Acetone, 4:1, v/v). NMR spectra are in good agreement with the literature.14
The NMR spectra are in good agreement with the litera- 1H NMR (500MHz, CDCl3): δ=7.63 (s, 1H), 7.56 (d,
ture.67 1H NMR (600MHz, CDCl3): δ=8.38 (d, J=8.2Hz, J=8.2Hz, 1H), 7.47 (d, J=7.8Hz, 1H), 7.40 (dd, J=7.2,
1H), 7.98 (d, J=8.2Hz, 1H), 7.95 (s, 1H), 7.91 (d, J=8.6Hz, 1.5Hz, 1H), 7.36−7.31 (m, 3H), 7.31−7.27 (m, 2H), 2.33
1H), 7.76−7.70 (m, 3H), 7.66−7.62 (m, 1H), 7.54 (m, 3H), (s, 3H). 13C NMR (151MHz, CDCl3): δ=155.2, 142.3,
7.42 (t, J=7.4Hz, 1H). 13C NMR (151MHz, CDCl3): 137.0, 131.0, 130.6, 130.5, 128.0, 126.0, 124.5, 122.9,
δ=151.6, 140.7, 132.4, 131.7, 129.2, 128.4, 127.8, 127.6, 121.5, 120.8, 111.7, 20.6. IR(KBr): υmax =3061, 2924,
126.6, 125.5, 123.8, 123.7, 122.1, 121.8, 120.3, 118.9. 2853, 1606, 1488, 1452, 1379, 1332, 1219, 1103, 1086,
IR(KBr): υmax =3053, 1603, 1561, 1518, 1444, 1386, 1246, 1008, 962, 857, 774, 747, and 723cm−1. MS (ESI):
1218, 1127, 1068, 1026, 918, 867, 810, 790, 757, 742, 695, m/z=209.14, (100) (M+H)+.
631, and 565cm−1. MS (ESI): m/z=245.08, (100) (M+H)+.
3-(m-Tolyl)benzofuran (2ac): Colorless oil. The NMR
1-Phenylnaphtho[2,1-b]furan (2n): Colorless oil. The spectra are in good agreement with the literature.64 1H
NMR spectra are in good agreement with the literature.68 NMR (500MHz, CDCl3): δ=7.85 (d, J=7.3Hz, 1H), 7.78
1H NMR (600MHz, CDCl3): δ=8.07 (d, J=8.4Hz, 1H), (s, 1H), 7.55 (d, J=8.0Hz, 1H), 7.46 (d, J=7.1Hz, 2H),
7.99 (d, J=8.1Hz, 1H), 7.81 (d, J=9.0Hz, 1H), 7.77−7.72 7.36 (dt, J=9.2, 4.6Hz, 2H), 7.31 (td, J=7.6, 0.9Hz, 1H),
(m, 2H), 7.66 (dt, J=3.3, 1.9Hz, 2H), 7.59−7.54 (m, 2H), 7.20 (d, J=7.5Hz, 1H), 2.44 (s, 3H). 13C NMR (151MHz,
7.54−7.50 (m, 1H), 7.48 (ddd, J=8.1, 7.0, 1.2Hz, 1H), CDCl3): δ=155.9, 141.4, 138.8, 132.1, 129.0, 128.39,
7.41 (ddd, J=8.2, 6.9, 1.3Hz, 1H). 13C NMR (151MHz, 128.35, 126.7, 124.8, 124.6, 123.1, 122.5, 120.6, 111.9,
CDCl3): δ=153.3, 141.8, 133.3, 131.0, 130.0, 129.1, 128.7, 21.7. IR(KBr): υmax =3034, 2920, 1609, 1452, 1336, 1234,
128.5, 128.0, 126.1, 126.1, 124.6, 124.5, 123.5, 120.9, 1188, 1108, 1012, 857, 833, 783, 768, 744, 699, and
112.8. IR(KBr): υmax =3051, 1524, 1488, 1443, 1384, 1294, 614cm−1. MS (ESI): m/z=209.11, (100) (M+H)+.
1251, 1224, 1110, 993, 947, 858, 803, 754, 700, 634, 611,
3-(p-Tolyl)benzofuran (2ad): Yellow oil. The NMR
559, and 517cm−1. MS (ESI): m/z=245.07, (100) (M+H)+. spectra are in good agreement with the literature.14 1H
3-Phenyl-4H-furo[3,2-c]chromen-4-one (2o): White NMR (600MHz, CDCl3): δ=7.84 (dd, J=7.7, 0.6Hz, 1H),
crystal, m.p. 162°C–164°C (Lit69 177°C) (PE/EA, 4:1, v/v). 7.77 (s, 1H), 7.58−7.53 (m, 3H), 7.38−7.33 (m, 1H),
The NMR spectra are in good agreement with the litera- 7.32−7.29 (m, 3H), 2.43 (s, 3H). 13C NMR (151MHz,
ture.69 1H NMR (600MHz, CDCl3): δ=7.92 (dd, J=7.8, CDCl3): δ=155.9, 141.2, 137.4, 129.8, 129.2, 127.5, 126.8,
1.5Hz, 1H), 7.78 (s, 1H), 7.76 (d, J=1.6Hz, 2H), 7.57−7.51 124.6, 123.0, 122.3, 120.6, 111.9, 21.4. IR(KBr):
(m, 1H), 7.46 (t, J=7.6Hz, 3H), 7.42−7.34 (m, 2H). 13C
υmax =3026, 2920, 1578, 1508, 1452, 1342, 1307, 1220,
NMR (151MHz, CDCl3): δ=159.0, 158.0, 152.8, 141.4, 1209, 1108, 1092, 1012, 964, 857, 824, 796, 769, 745, 565,
131.1, 129.2, 128.8, 128.7, 128.5, 126.9, 124.6, 121.1, 516, and 421cm−1. MS (ESI): m/z=209.32, (100) (M+H)+.
117.3, 113.0, 108.7. IR(KBr): υmax =3150, 3052, 1740,
3-(4-Fluorophenyl)benzofuran (2ae): Yellow oil. The
1629, 1594, 1543, 1497, 1487, 1449, 1414, 1366, 1317, NMR spectra are in good agreement with the literature.14
1286, 1249, 1213, 1155, 1101, 1072, 1045, 966, 927, 888, 1H NMR (600MHz, CDCl3): δ=7.81−7.77 (m, 1H), 7.76
793, 753, 722, 695, 632, 612, and 523cm−1. MS (ESI): (s, 1H), 7.63−7.58 (m, 2H), 7.57−7.55 (m, 1H), 7.37 (m,
m/z=263.06, (100) (M+H)+.
1H), 7.34−7.30 (m, 1H), 7.20−7.15 (m, 2H). 13C NMR
9-Phenyl-2H-furo[2,3-h]chromen-2-one (2p): Pale yel- (151MHz, CDCl3): δ=162.4 (d, J=246.6Hz), 155.9,
low needles, m.p. 112°C–114°C (PE/Acetone, 4:1, v/v). 1H 141.3, 129.2 (d, J=8.0Hz), 128.2 (d, J=3.3Hz), 126.5,
NMR (500MHz, CDCl3): δ=7.80 (d, J=9.6Hz, 1H), 124.8, 123.2, 121.5, 120.3, 116.1 (d, J=21.5Hz), 112.0.