Helvetica Chimica Acta – Vol. 96 (2013)
1321
(125 MHz): 7.1; 13.9; 22.4; 27.3; 34.0; 75.4; 122.6; 129.58; 129.63; 133.8; 148.8 (2 C); 161.8. MS: 421
([M þ Na]þ).
2-Iodohexyl 3,5-Dinitrobenzoate (8b). Minor product. Colorless liquid. IR (neat): 2924, 1731, 1626,
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1544, 1458, 1345, 1275, 1164, 1076, 922, 724. H-NMR (500 MHz): 0.95 (t, J ¼ 7.2, 3 H); 1.36 – 1.48 (m,
4 H); 1.85 – 1.91 (m, 4 H); 4.34 – 4.36 (m, 1 H); 4.60 – 4.70 (m, 2 H); 9.20 (s, 2 H); 9.26 (s, 1 H). 13C-NMR
(125 MHz): 13.8; 21.9; 29.5; 31.4; 36.2; 71.1; 122.6; 129.4; 129.5; 133.5; 148.8 (2 C); 161.9. MS: 421 ([M þ
Na]þ).
1-(Iodomethyl)hepthyl 3,5-Dinitrobenzoate (9a). Colorless liquid. IR (neat): 2925, 1732, 1627, 1597,
1548, 1461, 1419, 1345, 1274, 1161, 1131, 1076, 998, 966, 922, 824, 770, 724, 646. 1H-NMR (200 MHz): 0.95
(t, J ¼ 6.0, 3 H); 1.25 – 2.37 (m, 10 H); 3.50 (dd, J ¼ 5.8, 11.0, 2 H); 5.14 (m, 1 H); 9.19 (s, 2 H); 9.23 (s,
1 H). 13C-NMR (125 MHz): 7.1; 14.0; 22.5; 25.1; 28.9; 31.6; 34.2; 75.4; 122.6; 129.6 (2 CH); 133.7; 148.7
(2 C); 161.8. MS: 452.22 ([M þ 2]þ).
2-Iodo-1-phenylethyl Benzoate (10a). White solid. M.p. 128.38. IR (neat): 2923, 1725, 1603, 1506,
1454, 1153, 1107, 1089, 763, 698. 1H-NMR (500 MHz): 3.57 – 3.65 (m, 2 H); 6.09 (dd, J ¼ 5.2, 12.9, 1 H);
7.35 – 7.39 (m, 3 H); 7.42 – 7.48 (m, 4 H); 7.55 – 7.58 (m, 1 H); 8.13 (d, J ¼ 8.47, 2 H). 13C-NMR (100 MHz):
8.0; 75.4; 126.4 (2 CH); 128.4 (2 CH); 128.6 (2 CH); 129.5; 129.6; 129.7 (2 CH); 133.2; 138.4; 165.1. MS:
354.8 ([M þ 2]þ).
2-Iodo-1-phenylethyl 4-Fluorobenzoate (11a). Oil. IR (neat): 1725, 1603, 1506, 1356, 1265, 1178,
1153, 1107, 910, 853, 763. 1H-NMR (200 MHz): 3.53 – 3.68 (dd, J ¼ 5.6, 10.8, 2 H); 6.05 (dd, J ¼ 5.7, 12.8,
1 H); 7.11 (d, J ¼ 8.7, 1 H); 7.13 (d, J ¼ 8.4, 1 H); 7.34 – 7.42 (m, 5 H); 8.13 (d, J ¼ 8.7, 1 H); 8.15 (d, J ¼ 8.6,
1 H). 13C-NMR (100 MHz): 7.9; 75.7; 115.6; 115.8; 126.0; 126.3; 128.8; 128.78; 128.82; 132.4; 132.5; 138.4;
164.3; 164.7; 167.2. MS: 393.11 ([M þ Na]þ).
2-Iodo-1-phenylethyl 2-Hydroxybenzoate (12a). White gummy liquid. IR (neat): 2922, 1676, 1612,
1585, 1463, 1411, 1293, 1247, 1208, 1156, 1133, 1086, 1030, 794, 698, 670. 1H-NMR (200 MHz): 3.54 – 3.64
(m, 2 H); 6.10 (dd, J ¼ 5.5, 12.9, 1 H); 6.91 – 7.00 (m, 2 H); 7.41 – 7.53 (m, 6 H); 8.04 (dd, J ¼ 1.16, 8.0,
1 H); 10.52 (m, 1 H). 13C-NMR (100 MHz): 7.3; 76.1; 112.0; 117.7; 119.3; 125.9 (2 CH); 126.5; 128.8
(2 CH); 130.0; 136.1; 138.1; 161.5; 167.6. MS: 352.3 (Mþ).
2-Iodo-1-phenylethyl 3,4,5-Tris(acetyloxy)benzoate (13a). White solid. M.p. 140.68. IR (neat): 2939,
1781, 1726, 1427, 1370, 1325, 1242, 1053, 945, 851, 700. 1H-NMR (200 MHz): 2.31 (br. s, 9 H); 3.51 – 3.61
(m, 2 H); 6.06 (dd, J ¼ 5.5, 13.2, 1 H); 7.37 (br. s, 5 H); 7.86 (s, 2 H). 13C-NMR (100 MHz): 7.3; 20.2
(2 Me); 20.6; 76.4; 122.5 (2 CH); 126.3 (2 CH); 128.0; 128.9 (2 CH); 129.0; 138.0; 143.5; 163.2; 166.4;
167.6. MS: 548.8 ([M þ Na]þ).
2-Iodo-1-phenylethyl Pyridine-4-carboxylate (14a). White gummy mass. IR (neat): 3063, 1716, 1591,
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1494, 1477, 1453, 1120, 1328, 1275, 1180, 1110, 1041, 1024, 1001, 945, 828, 739, 698, 642, 580. H-NMR
(200 MHz): 3.52 – 3.61 (m, 2 H); 6.16 (dd, J ¼ 5.4, 7.5, 1 H); 7.27 – 7.52 (m, 5 H); 8.38 (d, J ¼ 6.2, 1 H); 8.82
(d, J ¼ 6.3, 1 H); 9.32 (br. s, 2 H). 13C-NMR (125 MHz): 7.7; 76.3; 123.6; 125.9; 127.3; 127.4; 128.7; 128.9;
129.1; 137.6; 137.9; 150.8; 153.5; 164.0. MS: 354.75 ([M þ 1]þ).
2-Iodo-1-phenylethyl 4-(Acetylsulfanyl)benzoate (15a). White solid. M.p. 110.38. IR (neat): 3063,
3062, 1731, 1595, 1566, 1494, 1454, 1415, 1397, 1353, 1261, 1210, 1179, 1102, 1053, 1516, 1002, 949, 944, 759,
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729, 666, 644, 614, 582. H-NMR (200 MHz): 2.46 (s, 3 H); 3.54 – 3.63 (m, 2 H); 6.09 (dd, J ¼ 6.7, 13.0,
1 H); 7.39 (s, 5 H); 7.52 (d, J ¼ 7.8, 2 H); 8.15 (d, J ¼ 7.8, 2 H). 13C-NMR (100 MHz): 7.8; 30.4; 75.8; 126.3
(2 CH); 128.6 (2 CH); 128.8; 130.1 (2 CH); 130.5; 134.0; 134.1 (2 CH); 138.3; 164.4; 192.4. MS: 448.8
([M þ Na]þ).
2-Iodo-1-phenylethyl 2-(Acetylamino)benzoate (16a). Yellow semisolid. IR (neat): 2924, 1689, 1588,
1525, 1447, 1364, 1296, 1257, 1164, 1140, 1083, 1049, 1003, 951, 756, 700, 651, 581, 554. 1H-NMR
(500 MHz): 2.18 (s, 3 H); 3.56 – 3.64 (m, 2 H); 6.06 (dd, J ¼ 6.7, 13.0, 1 H); 7.15 (dd, J ¼ 1.0, 8.2, 1 H);
7.36 – 7.39 (m, 5 H); 7.56 (dd, J ¼ 8.1, 1.6, 1 H); 8.23 (dd, J ¼ 8.0, 1.6, 1 H); 8.70 (d, J ¼ 8.4, 1 H). 13C-NMR
(125 MHz): 8.2; 26.3; 77.0; 115.0; 121.1; 123.3; 126.9 (2 CH); 129.7 (2 CH); 129.8; 131.7; 135.9; 138.9;
142.6; 167.7; 169.8. MS: 431.7 ([M þ Na]þ).
2-Iodo-1-phenylethyl Formate (17a). Colorless semisolid. IR (neat): 2924, 1725, 1604, 1494, 1453,
1414, 1296, 1051, 1023, 936, 761, 699, 644, 575, 539. 1H-NMR (200 MHz): 3.38 – 3.53 (m, 2 H); 5.97 (dd,
J ¼ 6.3, 13.2, 1 H); 7.33 (br. s, 5 H); 8.08 (s, 1 H). 13C-NMR (125 MHz): 7.8; 75.0; 126.4 (2 CH); 128.5
(2 CH); 128.8; 138.0; 159.8. MS: 276.6 (Mþ).