J. S. Yadav et al.
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CDCl3): d 3.89 (s, 3H), 5.55 (s, 1H), 6.79 (d, 1H, J 8.0 Hz ),
6.95 (d, 1H, J 2.1 Hz), 6.98 (dd, 2H, J 8.0, 2.1 Hz). EIMS: m/
CDCl3): d 142.7, 136.3, 129.2, 126.7, 112.8, 68.6; EIMS: m/z
(%) 234 (M , 19), 108 (100), 77 (21), 65 (59).
z (%) 204 (M , 100), 202 (98), 189 (74), 187 (72), 171 (34), 161
1-Iodo-3,4-dimethoxybenzene (3b', Table 1): Solid, mp 76
788C, IR (KBr): n 2938, 2836, 1573, 1478, 1432, 1409, 1293,
1227, 1220, 1179, 1134, 1010, 920, 837, 796, 774, 693 cmÀ1;
1H NMR (200 MHz, CDCl3): d 3.83 (s, 3H, OCH3), 3.87 (s,
3H, OCH3) 6.60 (d, 1H J 8.0 Hz), 7.21 (d, 1H, J 2.1 Hz) 7.23
(dd, 1H, J 8.0, 2.1 Hz); 13C NMR (CDCl3): d 146.4, 126.8,
(38), 159 (41), 91 (34), 75 (53), 51 (35).
2-Bromo-4-isopropylphenol (3j, Table 1): Liquid, IR (neat):
n 3507, 2962, 2872, 2361, 1711, 1606, 1559, 1496, 1476, 1414,
1364, 1324, 1276, 1184, 1039, 873, 848, 823, 735, 670 cmÀ1;
1H NMR (200 MHz, CDCl3): d 1.22 (s, 3H), 1.28 (s, 3H),
2.75 2.90 (m, 1H), 6.93 (d, 1H, J 8.1 Hz ), 7.05 7.12 (dd, 1H,
121.2, 118.7, 116.57.6. 56.8; EIMS: m/z (%) 264 (M 21), 137
J 8.1, 2.0 Hz), 7.28 (s, 1H); EIMS: m/z (%) 215 (M , 11), 172
(68), 122 (13), 106 (100), 75 (42), 50 (29).
(19), 91(56), 74 (41), 43 (100).
1-Iodo-3,4-methylenedioxybenzene (3c', Table 1): Liquid,
IR (neat): n 2938, 2843, 1676, 1506, 1480, 1437, 1374, 1295,
2-Bromo-4,5-methylenedioxyphenol (3k, Table 1): Solid,
mp 150 1528C, IR (KBr): n 3489, 2924, 2854, 1619, 1469,
1229, 1126, 1046, 1010, 949, 848, 774, 650 cmÀ1 1H NMR
;
1379, 1164, 1014, 963, 827, 650 cmÀ1
;
1H NMR (200 MHz,
(200 MHz, CDCl3): d 5.93 (s, 2H ), 6.58 (d, 1H, J 8.1 Hz),
CDCl3): d 5.30 (br s, 1H, OH), 5.92 (s, 2H), 6.58 (s, 1H), 6.88
7.12 (d, 1H, J 2.0, Hz). 7.18 (dd, 1H, J 8.1, 2.0 Hz); EIMS:
(s, 1H); EIMS: m/z (%) 217 (M , 28), 187 (11), 106 (100), 90
m/z (%) 248 (M , 34), 218 (12), 91 (67), 75 (100), 51 (42).
(48), 74 (69), 50 (31).
2-Iodo-4,5-dimethoxyacetophenone (3d', Table 1): Liquid,
IR (neat): n 2926, 2849, 1690, 1593, 1506, 1426, 1374, 1259,
1220, 1173, 1013, 775, 650 cmÀ1; 1H NMR (200 MHz, CDCl3):
d 2.48 (s, 3H), 3.88 (s, 3H), 3.89 (s, 3H), 6.79 (d, 1H, J
5-Bromo-2-hydroxybenzaldehyde (3l, Table 1): Solid, mp
104 1058C, IR (KBr): n 3226, 2876, 2364, 1673, 1610, 1563,
1467, 1373, 1305, 1276, 1207, 1155, 1114, 890, 828, 766, 697,
1
624 cmÀ1; H NMR (200 MHz, CDCl3): d 6.90 (d, 1H, J
8.0 Hz), 7.48 (m, 1H); EIMS: m/z (%) 306 (M , 36), 275 (21),
8.0 Hz), 7.60 (dd, 1H, J 8.0, 2.0 Hz), 7.70 (s, 1H), 9.95 (s,
260 (12), 133 (74), 90 (57), 74 (100), 50 (41).
1H, -CHO), 10.9 (br s, 1H, OH); EIMS: m/z (%) 201 (M , 95),
5-Iodovaniline (3e', Table 1): Solid, mp 180 1828C, IR
(KBr): n 3504, 2961, 2843, 1706, 1630, 1592, 1520, 1467, 1396,
1273, 1215, 1185, 1094, 1016, 950, 865, 758, 650 cmÀ1; 1H NMR
(200 MHz, CDCl3): d 3.96 (s, 3H), 6.65 (br s, 1H, OH), 7.36
(d, 1H, J 2.0 Hz). 7.84 (d, 1H, J 2.0 Hz), 9.80 (s, 1H, CHO);
13C NMR (50 MHz, CDCl3): d 188.2, 150.6, 145.8, 132.5,
200 (100), 157 (12), 144 (16), 65 (34 ), 63 (38), 43 (21).
1-Bromo-2-methylnaphthalene (3m, Table 1): Liquid, IR
(neat): n 3052, 2979, 2867, 2361, 1714, 1595, 1556, 1501, 1440,
1326, 1259, 1221, 1138, 1034, 964, 898, 862, 808, 763, 642 cmÀ1;
1H NMR (200 MHz, CDCl3): d 2.65 (s, 3H), 7.30 (d, 1H, J
8.1 Hz ), 7.55 (d, 1H, J 8.0 Hz), 7.60 (dd, 1H, J 8.1, 2.0 Hz),
7.70 (m, 1H), 7.80 (d, 1H, J 8.1 Hz), 8.30 (d, 1H, J 8.0 Hz);
128.3, 108.2, 82.6, 54.3; EIMS: m/z (%) 278 (M , 20), 246 (57),
119 (70), 90 (100), 74 (36), 50 (31).
EIMS: m/z (%) 221 (M 19), 142 (100), 126 (14), 116 (20), 91
1,3-Dimethoxy-2-methyl-4-iodobenzene (3f', Table 1): Liq-
uid, IR (neat): n 2943, 2857, 1685, 1597, 1523, 1478, 1421,
1349, 1284, 1213, 1179, 1084, 1018, 935, 867, 794, 658 cmÀ1;
1H NMR (200 MHz, CDCl3): d 2.20 (s, 3H), 3.79 (s, 3H), 3.80
(s, 3H), 6.40 (d 1H, J 8.0 Hz). 7.50 (d, 1H, J 8.0 Hz); EIMS:
(31), 43 (20).
1-Bromo-2-methoxynaphthalene (3n, Table 1): Liquid, IR
(neat): n 2978, 2843, 1604, 1574, 1469, 1423, 1294, 1225, 1180,
1093, 1022, 920, 893, 859, 809, 766, 652 cmÀ1 1H NMR
;
(200 MHz, CDCl3): d 3.98 (s, 3H), 7.26 (d, 1H, J 8.0 Hz),
7.39 7.41 (m, 1H), 7.54 7.56 (m, 1H), 7.72 (d, 1H, J 7.9 Hz),
7.80 (d, 1H, J 8.0 Hz), 8.22 (d, 1H, J 7.9 Hz ); EIMS: m/z
m/z (%) 278 (M , 72), 247 (27), 232 (10), 105 (100), 90 (60), 66
(11), 50 (30).
1-Bromo-2-iodo-4,5-dimethoxybenzene (3g', Table 1): Sol-
id, mp 89 918C, IR (KBr): n 2957, 2836, 1605, 1572, 1468,
1416, 1297, 1223, 1179, 1091, 1023, 927, 861, 784, 690 cmÀ1;
1H NMR (200 MHz, CDCl3): d 3.85 (s, 3H), 3.86 (s, 3H), 7.12
(%) 237 (M , 19), 206 (41), 194 (11), 181 (28), 157 (12), 130
(15), 126 (100), 114 (23), 104 (58), 102 (32), 76 (69), 51 (20).
1-Bromo-4-methoxynaphthalene (3o, Table 1): Liquid, IR
(neat): n 2959, 2847, 1608, 1571, 1465, 1427, 1291, 1223, 1182,
(s, 1H), 7.23 (s, 1H); EIMS: m/z (%) 344 (M , 92), 342 (100),
1091, 1026, 923, 891, 861, 812, 765, 650 cmÀ1
;
1H NMR
329 (31), 327 (57), 311 (12), 296 (23), 169 (53), 89 (31), 74 (32),
50 (29).
(200 MHz, CDCl3): d 3.92 (s, 3H), 6.61 (d, 1H, J 7.9 Hz),
7.53 (m, 1H), 7.59 (m, 1H), 7.62 (d, 1H, J 8.0 Hz), 8.14 (d, 1H,
1,2,3-Trimethoxy-4-iodobenzene (3h', Table 1): Liquid, IR
J 7.9 Hz), 8.25 (d, 1H, J 8.0 Hz); EIMS: m/z (%) 237 (M ,
(neat): n 2937, 2838, 1572, 1476, 1430, 1405, 1292, 1221, 1176,
28), 222 (16), 206 (38), 194 (19), 181 (25), 157 (13), 126 (100),
114 (20), 104 (39), 76 (48), 51 (30).
1132, 1091, 1009, 918, 834, 794, 772, 690 cmÀ1 1H NMR
;
(200 MHz, CDCl3): d 3.79 (s, 3H), 3.80 (s, 3H), 3.85 (s, 3H),
1-Bromo-2-naphthol (3p, Table 1): Solid, mp 79 808C, IR
(KBr): n 3498, 2983, 2848, 1615, 1583, 1511, 1476, 1410, 1286,
1217, 1181, 1083, 1026, 931, 893, 866, 817, 768, 665 cmÀ1;
1H NMR (200 MHz, CDCl3): d 7.91 (d, 1H, J 8.1 Hz),
6.51 (d, 1H, J 8.0 Hz). 7.42 (d, 1H, J 8.0 Hz); EIMS: m/z
(%) 294 (M , 100), 179 (10), 109 (12), 77 (10).
2-Methoxy-4-iodophenol (3i', Table 1): Liquid, IR (neat):
n 3497, 2963, 2847, 1604, 1582, 1478, 1423, 1296, 1221, 1187,
1095, 1038, 927, 867, 793, 685 cmÀ1; 1H NMR (200 MHz,
7.72 7.74 (m, 2H), 7.56 (t, 1H, J 8.2 Hz), 7.41 (t, 1H, J
8.2 Hz), 7.28 (d, 1H, J 8.1 Hz ); EIMS: m/z (%) 223 (M , 63),
CDCl3): d 3.90 (s, 3H), 5.42 (s, 1H, OH), 6.78 (d, 1H, J
194 (36), 168 (21), 148 (18), 114 (100), 88 (19), 76 (59), 64 (27),
51 (30).
8.2 Hz), 6.90 7.00 (m, 2H); EIMS: m/z (%) 250 (M , 42), 218
(100), 91 (67), 75 (30), 51 (18).
1-Iodo-4-methoxybenzene (3a', Table 1): Colorless solid,
m p 51 528C, IR (KBr): n 2939, 2837, 1659, 1606, 1518, 1473,
1429, 1297, 1221, 1176, 1094, 1027, 929, 749, 692, 671 cmÀ1; 1H
NMR (200 MHz, CDCl3): d 3.80 (s, 3H, OCH3 ), 6.58 (d, 2H,
J 8.1 Hz), 7.48 (d, 2H J 8.1 Hz); 13C NMR (200 MHz,
4-Isopropyl-6-iodophenol (3j', Table 1): Liquid, IR (neat):
n 3506, 2961, 2874, 2363, 1709, 1607, 1558, 1493, 1473, 1416,
1361, 1322, 1278, 1183, 1037, 871, 846, 823, 736, 675 cmÀ1;
1H NMR (200 MHz, CDCl3): d 1.20 (s, 3H,), 1.22 (s, 3H), 2.80
(q, 1H J 7.0 Hz), 6.90 (d, 1H, J 8.0 Hz), 7.08 (dd, 1H, J
80
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Adv. Synth. Catal. 2004, 346, 77 82