The Journal of Organic Chemistry
Article
CDCl3): δ 196.5, 143.3, 138.0, 134.9, 132.2, 130.3, 130.0, 129.0, 128.2,
21.7.
1-Benzoylnaphthalene (3n).19g Colorless oil (654 mg, 94%). IR
(neat): 3058, 2926, 1659, 1597, 1578, 1507, 1448, 1315, 1282, 1249,
1206, 912, 775, 712 cm−1. 1H NMR (400 MHz, CDCl3): δ 8.09 (d, J =
7.6 Hz, 1H), 7.95 (d, J = 8.4 Hz, 1H), 7.89−7.83 (m, 3H), 7.56−7.37
(m, 7H). 13C NMR (100 MHz, CDCl3): δ 198.0, 138.4, 136.5, 133.8,
133.3, 131.3, 131.1, 130.5, 128.5, 128.4, 127.8, 127.3, 126.5, 125.8,
124.4.
4-Methoxybenzophenone (3d).19g White solid (471 mg, 74%). Mp
59−60 °C. IR (KBr): 3061, 2934, 1651, 1599, 1508, 1446, 1258, 1172,
1
844, 742, 701 cm−1. H NMR (400 MHz, CDCl3): δ 7.85−7.82 (m,
2H), 7.77−7.74 (m, 2H), 7.58−7.54 (m, 1H), 7.47 (t, J = 7.6 Hz, 2H),
6.96 (dd, J = 8.8, 2.0 Hz, 2H), 3.88 (s, 3H). 13C NMR (100 MHz,
CDCl3): δ 195.6, 163.2, 138.3, 132.6, 131.9, 130.1, 129.8, 128.2, 113.6,
55.5.
2-Benzoylnaphthalene (3o).19g White solid (641 mg, 92%). Mp
77−78 °C. IR (KBr): 3056, 1657, 1594, 1497, 1446, 1272, 1116, 819,
1
754, 698 cm−1. H NMR (400 MHz, CDCl3): δ 8.24 (s, 1H), 7.95−
4-Chlorobenzophenone (3e).14f White solid (604 mg, 93%). Mp
75−76 °C. IR (KBr): 1651, 1597, 1585, 1285, 1137, 1070, 955, 729,
7.82 (m, 6H), 7.61−7.45 (m, 5H). 13C NMR (100 MHz, CDCl3): δ
196.7, 138.0, 135.3, 134.9, 132.4, 132.3, 131.9, 130.1, 129.5, 128.4,
128.3, 127.9, 126.8, 125.8.
1
696 cm−1. H NMR (400 MHz, CDCl3): δ 7.79−7.74 (m, 4H), 7.60
(t, J = 7.4 Hz, 1H), 7.52−7.44 (m, 4H). 13C NMR (100 MHz,
CDCl3): δ 195.5, 138.9, 137.2, 135.9, 132.7, 131.5, 130.0, 128.7, 128.4.
4-Nitrobenzophenone (3f).14f Yellow solid (586 mg, 86%). Mp
136−137 °C. IR (KBr): 3101, 1652, 1595, 1578, 1515, 1358, 1318,
1278, 852, 706, 693 cm−1. 1H NMR (400 MHz, CDCl3): δ 8.35 (d, J =
8.8 Hz, 2H), 7.95 (d, J = 8.4 Hz, 2H), 7.81 (d, J = 8.4 Hz, 2H), 7.66 (t,
J = 7.2 Hz, 1H), 7.53 (t, J = 7.8 Hz, 2H). 13C NMR (100 MHz,
CDCl3): δ 194.8, 149.8, 142.9, 136.3, 133.5, 130.7, 130.1, 128.7, 123.6.
4-Cyanobenzophenone (3g).14h White solid (553 mg, 89%). Mp
110−112 °C. IR (KBr): 2229, 1651, 1592, 1579, 1404, 1312, 1282,
1067, 857, 736, 696 cm−1. 1H NMR (400 MHz, CDCl3): δ 7.88 (d, J =
8.8 Hz, 2H), 7.81−7.77 (m, 4H), 7.65 (t, J = 7.6 Hz, 1H), 7.52 (t, J =
7.6 Hz, 2H). 13C NMR (100 MHz, CDCl3): δ 194.5, 140.7, 135.9,
132.8, 131.7, 129.7, 129.5, 128.1, 117.5, 115.2.
2-Benzoylthiophene (3p).19g White solid (502 mg, 89%). Mp 54−
55 °C. IR (KBr): 1634, 1599, 1577, 1447, 1413, 1290, 910, 843, 729
cm−1. 1H NMR (400 MHz, CDCl3): δ 7.88−7.85 (m, 2H), 7.74−7.71
(m, 1H), 7.66−7.64 (m, 1H), 7.60 (t, J = 7.4 Hz, 1H), 7.50 (t, J = 7.6
Hz, 2H), 7.18−7.15 (m, 1H). 13C NMR (100 MHz, CDCl3): δ 188.2,
143.7, 138.2, 134.8, 134.2, 132.3, 129.2, 128.4, 128.0.
3-Benzoylpyridine (3q).27 White solid (467 mg, 85%). Mp 39−41
°C. IR (KBr): 3058, 2923, 1660, 1415, 1282, 923, 713 cm−1. 1H NMR
(400 MHz, CDCl3): δ 9.02 (s, 1H), 8.83 (s, 1H), 8.13 (d, J = 8.0 Hz,
1H), 7.81 (d, J = 7.6 Hz, 2H), 7.64 (t, J = 7.4 Hz, 1H), 7.51 (t, J = 7.6
Hz, 2H), 7.48−7.44 (m, 1H). 13C NMR (100 MHz, CDCl3): δ 194.7,
152.5, 150.7, 137.3, 136.7, 133.2, 130.0, 128.6, 127.6, 123.5.
4,4′-Dimethylbenzophenone (3r).14g White solid (548 mg, 87%).
Mp 94−95 °C. IR (KBr): 1646, 1606, 1569, 1277, 1176, 926, 844, 752
4-Acetylbenzophenone (3h).24 White solid (612 mg, 91%). Mp
83−84 °C. IR (KBr): 1689, 1656, 1595, 1446, 1357, 1278, 931, 698
cm−1. 1H NMR (400 MHz, CDCl3): δ 8.06 (dd, J = 6.6, 1.8 Hz, 2H),
7.87 (dd, J = 6.6, 1.8 Hz, 2H), 7.81 (d, J = 7.6 Hz, 2H), 7.65−7.61 (m,
1H), 7.51 (t, J = 7.6 Hz, 2H), 2.68 (s, 3H). 13C NMR (100 MHz,
CDCl3): δ 197.5, 196.0, 141.4, 139.6, 136.9, 133.0, 130.1, 130.0, 128.5,
128.2, 26.9.
1
cm−1. H NMR (400 MHz, CDCl3): δ 7.70 (d, J = 8.0 Hz, 4H), 7.27
(d, J = 8.4 Hz, 4H), 2.44 (s, 6H). 13C NMR (100 MHz, CDCl3): δ
196.3, 142.9, 135.3, 130.2, 128.9, 21.6.
4-Chloro-4′-methylbenzophenone (3s).14g White solid (623 mg,
90%). Mp 128−129 °C. IR (KBr): 1645, 1607, 1585, 1287, 1147,
1087, 929, 854, 749 cm−1. 1H NMR (400 MHz, CDCl3): δ 7.74 (d, J =
8.4 Hz, 2H), 7.69 (d, J = 8.0 Hz, 2H), 7.45 (d, J = 8.8 Hz, 2H), 7.29
(d, J = 8.0 Hz, 2H), 2.45 (s, 3H). 13C NMR (100 MHz, CDCl3): δ
195.3, 143.5, 138.6, 136.2, 134.5, 131.4, 130.2, 129.1, 128.6, 21.7.
4-Methyl-4′-nitrobenzophenone (3t).14e Yellow solid (636 mg,
88%). Mp 120−122 °C. IR (KBr): 1653, 1600, 1563, 1521, 1353,
Methyl 4-Benzoylbenzoate (3i).24 White solid (634 mg, 88%). Mp
108−109 °C. IR (KBr): 1716, 1647, 1616, 1595, 1147, 1076, 826, 712
cm−1. 1H NMR (400 MHz, CDCl3): δ 8.15 (dd, J = 6.6, 1.8 Hz, 2H),
7.84 (dd, J = 6.8, 2.0 Hz, 2H), 7.81 (d, J = 8.0 Hz, 2H), 7.65−7.60 (m,
1H), 7.50 (t, J = 7.6 Hz, 2H), 3.97 (s, 3H). 13C NMR (100 MHz,
CDCl3): δ 196.0, 166.3, 141.3, 137.0, 133.2, 133.0, 130.1, 129.8, 129.5,
128.5, 52.5.
1
1315, 1145, 1078, 933, 853, 732 cm−1. H NMR (400 MHz, CDCl3):
δ 8.34 (d, J = 8.8 Hz, 2H), 7.92 (d, J = 8.8 Hz, 2H), 7.72 (d, J = 8.0
Hz, 2H), 7.33 (d, J = 8.0 Hz, 2H), 2.47 (s, 3H). 13C NMR (100 MHz,
CDCl3): δ 194.5, 149.7, 144.6, 143.4, 133.7, 130.5, 130.3, 129.4, 123.5,
21.7.
3-(Trifluoromethyl)benzophenone (3j).25 White solid (690 mg,
92%). Mp 50−51 °C. IR (KBr): 3068, 1667, 1611, 1598, 1337, 1268,
1
1171, 1128, 715 cm−1. H NMR (400 MHz, CDCl3): δ 8.07 (s, 1H),
4-Bromo-4′-chlorobenzophenone (3u).14e White solid (753 mg,
85%). Mp 146−148 °C. IR (KBr): 3056, 1646, 1586, 1289, 855, 753
7.98 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 7.6 Hz, 1H), 7.81−7.77 (m, 2H),
7.69−7.60 (m, 2H), 7.52 (t, J = 7.6 Hz, 2H). 13C NMR (100 MHz,
1
cm−1. H NMR (400 MHz, CDCl3): δ 7.72 (d, J = 8.4 Hz, 2H), 7.64
2
CDCl3): δ 195.1, 138.3, 136.8, 133.1, 133.0, 131.0 (q, JC−F = 36.4
(s, 4H), 7.47 (d, J = 8.4 Hz, 2H). 13C NMR (100 MHz, CDCl3): δ
194.4, 139.2, 136.0, 135.5, 131.8, 131.4, 131.3, 128.8, 127.8.
4,4′-Dichlorobenzophenone (3v).14e White solid (685 mg, 91%).
Mp 146−147 °C. IR (KBr): 1655, 1589, 1565, 1287, 1147, 1089, 852,
755 cm−1. 1H NMR (400 MHz, CDCl3): δ 7.73−7.71 (m, 4H), 7.48−
7.45 (m, 4H). 13C NMR (100 MHz, CDCl3): δ 194.2, 139.2, 135.5,
131.4, 128.8.
3
3
Hz), 130.0, 128.9, 128.8 (q, JC−F = 3.6 Hz), 128.6, 126.7 (q, JC−F
=
1
3.8 Hz), 123.5 (q, JC−F = 272.0 Hz).
2-Methylbenzophenone (3k).14f Colorless oil (488 mg, 83%). IR
(neat): 3062, 2927, 1664, 1598, 1579, 1449, 1268, 924, 732, 709 cm−1.
1H NMR (400 MHz, CDCl3): δ 7.80 (d, J = 7.6 Hz, 2H), 7.57 (t, J =
7.6 Hz, 1H), 7.45 (t, J = 7.6 Hz, 2H), 7.39 (t, J = 7.6 Hz, 1H), 7.33−
7.24 (m, 3H), 2.33 (s, 3H). 13C NMR (100 MHz, CDCl3): δ 198.1,
138.2, 137.3, 136.2, 132.6, 130.5, 129.7, 129.6, 128.0, 127.9, 124.7,
19.5.
4-Chloro-4′-nitrobenzophenone (3w).14e Yellow solid (675 mg,
86%). Mp 100−101 °C. IR (KBr): 1669, 1584, 1520, 1349, 1272,
1
1170, 1088, 929, 851, 738 cm−1. H NMR (400 MHz, CDCl3): δ
2-Methoxybenzophenone (3l).14d Colorless oil (401 mg, 63%). IR
(neat): 3061, 2945, 1667, 1599, 1581, 1487, 1294, 1245, 1023, 926,
8.37−8.35 (m, 2H), 7.93−7.91 (m, 2H), 7.77−7.75 (m, 2H), 7.52−
7.50 (m, 2H). 13C NMR (100 MHz, CDCl3): δ 193.6, 149.9, 142.5,
140.1, 134.5, 131.5, 130.6, 129.1, 123.7.
756, 703 cm−1. H NMR (400 MHz, CDCl3): δ 7.81 (d, J = 7.6 Hz,
1
4-Methoxy-4′-methylbenzophenone (3x).14g White solid (570 mg,
84%). Mp 88−89 °C. IR (KBr): 1645, 1598, 1505, 1316, 1261, 1169,
1147, 1023, 929, 849, 761 cm−1. 1H NMR (400 MHz, CDCl3): δ 7.81
(d, J = 8.8 Hz, 2H), 7.68 (d, J = 8.0 Hz, 2H), 7.27 (d, J = 8.4 Hz, 2H),
6.96 (d, J = 8.8 Hz, 2H), 3.89 (s, 3H), 2.44 (s, 3H). 13C NMR (100
MHz, CDCl3): δ 195.4, 163.1, 142.6, 135.5, 132.4, 130.5, 130.0, 128.9,
113.5, 55.5, 21.6.
2H), 7.55 (t, J = 7.4 Hz, 1H), 7.49−7.34 (m, 4H), 7.04 (t, J = 7.4 Hz,
1H), 6.99 (d, J = 8.4 Hz, 1H), 3.72 (s, 3H). 13C NMR (100 MHz,
CDCl3): δ 196.5, 157.4, 137.8, 133.0, 131.9, 129.8, 129.6, 128.9, 128.2,
120.5, 111.5, 55.6.
Methyl 2-Benzoylbenzoate (3m).26 White solid (627 mg, 87%).
Mp 50−52 °C. IR (KBr): 3064, 2952, 1728, 1653, 1597, 1280, 1084,
1
717 cm−1. H NMR (400 MHz, CDCl3): δ 8.04 (dd, J = 7.8, 1.0 Hz,
4-Chloro-4′-methoxybenzophenone (3y).14g White solid (658 mg,
89%). Mp 116−117 °C. IR (KBr): 1646, 1607, 1586, 1287, 1146,
1088, 930, 854, 749 cm−1. 1H NMR (400 MHz, CDCl3): δ 7.79 (d, J =
8.8 Hz, 2H), 7.70 (d, J = 8.4 Hz, 2H), 7.44 (d, J = 8.0 Hz, 2H), 6.96
1H), 7.74 (d, J = 8.0 Hz, 2H), 7.64 (dd, J = 7.6, 1.2 Hz, 1H), 7.62−
7.52 (m, 2H), 7.45−7.39 (m, 3H), 3.60 (s, 3H). 13C NMR (100 MHz,
CDCl3): δ 197.0, 166.4, 141.7, 137.2, 133.1, 132.4, 130.1, 129.6, 129.5,
129.3, 128.5, 127.8, 52.1.
F
J. Org. Chem. XXXX, XXX, XXX−XXX