Organic & Biomolecular Chemistry
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128.77, 128.63, 67.79; MS (EI, 70 eV) m/z: 212.10 (M+); IR (KBr): 7.1 Hz, 2 H), 2.42 (s, 3 H), 1.42 (t, J = 7.1 Hz, 3 H); 13C NMR
2983, 1739, 1690, 1598, 1520, 1451, 1373, 1343, 1244, 1195, (100 MHz, CDCl3) δ 186.70, 164.02, 138.85, 135.77, 130.29,
1173, 1048, 992, 749, 698 cm−1
.
128.78, 127.36, 62.28, 21.27, 14.11; MS (EI, 70 eV) m/z: 164.13
Ethyl 2-(4-methoxyphenylamino)-2-phenylacetate (P2a).7i (M+); IR (KBr): 2925, 2854, 1737, 1686, 1602, 1459, 1373, 1309,
Yellow oil; 23.1 mg, 45% yield; 1H NMR (400 MHz, CDCl3) 1231, 1154, 1093, 1031, 750, 674, 463 cm−1
δ 7.49 (d, J = 7.5 Hz, 2 H), 7.36–7.30 (m, 3 H), 6.72 (d, J = 8.8 Hz,
Ethyl 4-(trifluoromethyl)benzoate (3i).21 Yellow oil; 11.4 mg,
.
2 H), 6.53 (d, J = 8.7 Hz, 2 H), 5.00 (s, 1 H), 4.67 (s, 1 H), 29% yield; 1H NMR (400 MHz, CDCl3) δ 8.18 (d, J = 8.0 Hz,
4.25–4.11 (m, 2 H), 3.70 (s, 3 H), 1.20 (t, J = 7.1 Hz, 3 H); 13C 2 H), 7.80 (d, J = 8.1 Hz, 2 H), 4.49 (q, J = 7.1 Hz, 2 H), 1.46 (t,
NMR (100 MHz, CDCl3) δ (ppm) 172.1, 152.5, 140.3, 137.9, J = 7.1 Hz, 3 H); 13C NMR (100 MHz, CDCl3) δ 184.98, 162.80,
128.8, 128.2, 127.3, 114.8, 61.7, 61.6, 55.7, 14.1; MS (ESI): m/z = 136.02, 135.69, 135.28, 130.43, 125.91, 125.87, 62.76, 14.06; MS
286.6 [M+], 324.6 [M + K+]; IR (KBr): 3399, 2927, 2854, 1734, (ESI): m/z = 219.0 [M+]; IR (KBr): 2924, 2854, 2388, 2287, 1734,
1513, 1457, 1370, 1305, 1239, 1178, 1029, 820, 732, 688, 1697, 1603, 1411, 1374, 1323, 1202, 1170, 1016, 980, 843, 741,
523 cm−1
2-Diphenyl-ethane-1,2-dione (3a–1).24 Oil; 19.3 mg, 51%
.
591 cm−1
Ethyl 3-nitrobenzoate (3j).26 Yellow oil; 7.4 mg, 21% yield;
.
yield; 1H NMR (400 MHz, CDCl3) δ 7.97 (d, J = 7.4 Hz, 4 H), 1H NMR (400 MHz, CDCl3) δ 8.90 (s, 1 H), 8.58–8.46 (m, 2 H),
7.65 (t, J = 7.4 Hz, 2 H), 7.51 (t, J = 7.7 Hz, 4 H); 13C NMR 7.76 (t, J = 8.1 Hz, 1 H), 4.51 (q, J = 7.1 Hz, 2 H), 1.46 (t, J = 7.1
(100 MHz, CDCl3) δ 194.61, 134.91, 133.01, 129.91, 129.04. MS Hz, 3 H); 13C NMR (100 MHz, CDCl3) δ 183.54, 162.19, 137.59,
(EI, 70 eV) m/z: 210.12 (M+); IR (KBr): 3063, 1660, 1594, 1448, 135.45, 130.20, 128.84, 125.02, 63.06, 14.05; MS (ESI): m/z =
1321, 1275, 1209, 1173, 1071, 793, 750, 718, 641, 464 cm−1
Ethyl 4-methoxybenzoate (3d).21 Yellow oil; 30.5 mg, 94% 1531, 1407, 1343, 1311, 1196, 1099, 1021, 884, 857, 813, 700,
yield; 1H NMR (400 MHz, CDCl3) δ 8.00 (d, J = 8.8 Hz, 2 H), 673 cm−1
6.97 (d, J = 8.8 Hz, 2 H), 4.43 (q, J = 7.1 Hz, 2 H), 3.89 (s, 3 H),
4′-Methoxy-3-nitro-1,1′-biphenyl (3j–1).27 Yellow oil; 14.5 mg,
.
219.0 [M + Na+]; IR (KBr): 3087, 2925, 2854, 1732, 1696, 1611,
.
1.42 (t, J = 7.1 Hz, 3 H); 13C NMR (100 MHz, CDCl3) δ 184.90, 35% yield; 1H NMR (400 MHz, CDCl3) δ 8.43 (s, 1 H), 8.19–8.14
165.03, 164.18, 132.57, 125.51, 114.24, 62.16, 55.64, 14.12; MS (m, 1 H), 7.89 (d, J = 7.8 Hz, 1 H), 7.62–7.57 (m, 3 H), 7.04 (d,
(EI, 70 eV) m/z: 179.18 (M+); IR (KBr): 2933, 2846, 1736, 1676, J = 8.7 Hz, 2 H), 3.90 (s, 3 H); 13C NMR (100 MHz, CDCl3)
1599, 1572, 1463, 1308, 1266, 1207, 1164, 1021, 976, 841, 617, δ 160.10, 148.78, 142.49, 132.51, 131.10, 129.63, 128.28,
514 cm−1
Ethyl 3-methoxybenzoate (3e).25 Yellow oil; 26.3 mg, 81% IR (KBr): 2924, 2853, 1765, 1607, 1512, 1461, 1346, 1253, 1179,
yield; 1H NMR (400 MHz, CDCl3) δ 7.57 (d, J = 7.6 Hz, 1 H), 1044, 898, 875, 831, 749, 680, 570 cm−1
7.53 (s, 1 H), 7.41 (t, J = 7.9 Hz, 1 H), 7.20 (d, J = 8.2 Hz, 1 H),
Ethyl 4-chlorobenzoate (3k).21 Yellow oil; 22.5 mg, 68%
.
121.40, 121.37, 114.60, 55.43; MS (EI, 70 eV) m/z: 229.28 (M+);
.
4.45 (q, J = 7.1 Hz, 2 H), 3.86 (s, 3 H), 1.42 (t, J = 7.1 Hz, 3 H); yield; 1H NMR (400 MHz, CDCl3) δ 7.99 (d, J = 8.3 Hz, 2 H),
13C NMR (100 MHz, CDCl3) δ 186.33, 163.87, 133.70, 129.91, 7.49 (d, J = 8.3 Hz, 2 H), 4.45 (q, J = 7.1 Hz, 2 H), 1.43 (t, J =
123.11, 121.84, 113.28, 62.34, 55.51, 14.11; MS (ESI): m/z = 7.1 Hz, 3 H); 13C NMR (100 MHz, CDCl3) δ 184.86, 163.01,
200.09 [M + Na+]; IR (KBr): 2936, 2840, 1736, 1687, 1598, 1582, 135.25, 134.80, 134.07, 130.22, 129.87, 128.24, 62.66, 14.09; MS
1519, 1486, 1369, 1311, 1290, 1155, 1020, 875, 787, 677, (EI, 70 eV) m/z: 184.10 (M+); IR (KBr): 2925, 2854, 1736, 1689,
559 cm−1
Ethyl 2-methoxybenzoate (3f).21 Yellow oil; 13.6 mg, 42% 769, 673, 544, 482 cm−1
yield; 1H NMR (400 MHz, CDCl3) δ 7.88 (d, J = 7.7 Hz, 1 H), Ethyl 3-chlorobenzoate (3l).25 Yellow oil; 22.5 mg, 68%
.
1590, 1519, 1462, 1402, 1340, 1200, 1170, 1089, 1014, 976, 833,
.
7.59 (t, J = 7.9 Hz, 1 H), 7.07 (t, J = 7.5 Hz, 1 H), 6.99 (d, J = yield; 1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1 H), 7.92 (d, J =
8.4 Hz, 1 H), 4.39 (q, J = 7.1 Hz, 2 H), 3.87 (s, 3 H), 1.39 (t, J = 7.7 Hz, 1 H), 7.63 (d, J = 8.0 Hz, 1 H), 7.46 (t, J = 7.9 Hz, 1 H),
7.1 Hz, 3 H); 13C NMR (100 MHz, CDCl3) δ 186.60, 165.30, 4.46 (q, J = 7.1 Hz, 2 H), 1.43 (t, J = 7.1 Hz, 3 H); 13C NMR
136.27, 130.81, 121.32, 112.04, 61.76, 56.01, 14.13; MS (EI, (100 MHz, CDCl3) δ 184.86, 163.01, 135.25, 134.80, 130.22,
70 eV) m/z: 178.94 (M+); IR (KBr): 2929, 2843, 1739, 1674, 1599, 129.87, 128.24, 62.66, 14.09; MS (EI, 70 eV) m/z: 184.11 (M+); IR
1511, 1484, 1466, 1442, 1272, 1246, 1162, 1112, 1022, 979, 757, (KBr): 2926, 2854, 1737, 1693, 1510, 1570, 1424, 1370, 1343,
665, 530 cm−1
Ethyl 4-methylbenzoate (3g).21 Yellow oil; 26.0 mg, 88%
.
1308, 1192, 1023, 900, 782, 742 cm−1
.
Ethyl 4-fluorobenzoate (3m).21 Yellow oil; 17.3 mg, 57%
yield; 1H NMR (400 MHz, CDCl3) δ 7.91 (d, J = 8.0 Hz, 2 H), yield; H NMR (400 MHz, CDCl3) δ 8.12–8.06 (m, 2 H), 7.19 (t,
7.32 (d, J = 8.0 Hz, 2 H), 4.45 (q, J = 7.1 Hz, 3 H), 2.45 (s, 3 H), J = 8.5 Hz, 2 H), 4.45 (q, J = 7.1 Hz, 2 H), 1.43 (t, J = 7.1 Hz,
1.43 (t, J = 7.1 Hz, 2 H); 13C NMR (100 MHz, CDCl3) δ 186.11, 3 H); 13C NMR (100 MHz, CDCl3) δ 184.90, 163.22, 141.63,
164.05, 146.24, 130.15, 129.62, 62.22, 21.89, 14.11; MS (EI, 131.44, 129.31, 62.56, 14.09; MS (ESI): m/z = 192.9 [M + Na+];
70 eV) m/z: 164.10 (M+); IR (KBr): 2984, 2928, 1737, 1683, 1605, IR (KBr): 2926, 2854, 2361, 1736, 1689, 1598, 1507, 1414, 1372,
1448, 1412, 1371, 1304, 1203, 1173, 1118, 1017, 976, 867, 828, 1238, 1197, 1155, 1099, 1018, 978, 845, 747, 636, 549,
1
749, 618, 480 cm−1
Ethyl 3-methylbenzoate (3h).21 Yellow oil; 26.0 mg, 88%
.
506 cm−1
.
Ethyl
[1,1′-biphenyl]-4-carboxylate
(3n).28 Yellow
oil;
yield; 1H NMR (400 MHz, CDCl3) δ 7.80 (d, J = 7.0 Hz, 2 H), 33.4 mg, 82% yield; H NMR (400 MHz, CDCl3) δ 8.09 (d, J =
1
7.47 (d, J = 7.4 Hz, 1 H), 7.39 (t, J = 7.7 Hz, 1 H), 4.45 (q, J = 8.2 Hz, 2 H), 7.72 (d, J = 8.2 Hz, 2 H), 7.62 (d, J = 8.0 Hz, 2 H),
This journal is © The Royal Society of Chemistry 2013
Org. Biomol. Chem., 2013, 11, 6013–6022 | 6019