9
78
Tribromoisocyanuric Acid/Triphenylphosphine
J. Braz. Chem. Soc.
2
3
1
1
-bromooctane: bp 198 °C (lit: 201 °C); IR (KBr)
1169, 1099, 1052, 924, 751, 736, 640, 564, 539; H NMR
–
1
ν/cm 2958, 2927, 2855, 1466, 1439, 1378, 1256, 1099,
11, 723, 647, 564; H NMR (CDCl3, 200 MHz) δ 0.89 (t,
H, CH ), 1.28-1.45(m, 10 H, CH -(CH ) ), 1.81-1.91 (m,
H, CH -CH Br), 3.41 (t, 2H, CH Br); C NMR (CDCl ,
(CDCl , 200 MHz) δ 0.91 (d, 6H, CH ), 1.26-1.37 (m, 2H,
CH -CH(CH ) ), 1.49-1.69 (m, 1H, CH), 1.80-1.97 (m,
2H, CH -CH Br), 3.41 (t, 2H, CH Br); C NMR (CDCl ,
2 2 2 3
50 MHz) δ 22.6 (C5), 27.6 (C4), 31.0 (C3), 34.3 (C2), 37.6
3
3
1
9
3
2
5
2 3 2
13
3
3
2
5
13
2
2
2
3
+
+
0 MHz) δ 14.0 (C8), 22.6 (C7), 28.2 (C6), 28.7 (C5), 29.1
(C1); MS (70 eV) m/z 166 (M + 2), 164 (M ), 151, 149,
(
(
9
C4), 31.7 (C3), 32.8 (C2), 33.9 (C1); MS (70 eV) m/z 194
M + 2), 192 (M ), 151, 149, 137, 135, 123, 121, 109, 107,
5, 93, 71, 57, 43 (100%).
123, 121, 109, 107, 95, 93, 85, 69, 56, 43 (100%).
+
+
–1
2-bromo-4-methylpentane:IR (KBr) ν/cm 2983, 2960,
2
924, 2872, 2827, 1467, 1452, 1379, 1259, 1199, 1149,
24
1
1
-bromo-2-phenylethane: bp 218 °C (lit: 220-225 °C);
1051, 1001, 989, 921, 858, 813, 617, 540; H NMR (CDCl ,
3
–1
IR (KBr) ν/cm 3085, 3062, 3027, 2964, 2944, 2862, 1602,
200 MHz) δ 0.90 (d, 3H, CH CH), 0.92 (d, 3H, CH CH|),
3
3
1
9
584, 1496, 1454, 1431, 1314, 1262, 1215, 1196, 1030,
1.44-1.54 (m, 1H, CH(CH ) ), 1.71 (d, 3H, CH -CHBr),
3
2
3
1
13
19, 750, 699, 648, 542, 487; H NMR (CDCl , 200 MHz)
1.77-1.96 (m, 2H, CH ), 4.13-4.24 (m, 1H CHBr); C NMR
3
2
δ 3.18 (t, 2H, J 7.9, PhCH ), 3.59 (t, 2H, J 7.9, CH Br),
(CDCl , 50 MHz) δ 21.6 (C5), 22.9 (C5’), 26.9 (C4), 27.0
(C1), 50.2 (C2), 50.5 (C3); MS (70 eV) m/z 121 (M - iPr),
109, 107, 85, 69, 57, 55, 43 (100%).
2
1
2
3
3
+
7
3
1
1
.20-7.39 (m, 5H, CHarom); C NMR (CDCl , 50 MHz) δ
3
3.0 (CH Br), 39.6 (PhCH ), 127.1 (C ), 128.7 (Carom),
2
2
arom
+
28.9 (Carom), 139.1 (Carom); MS (70 eV) m/z 186 (M + 2),
+
+
84 (M ), 140, 105, 91 (100%), 77, 65, 51.
cyclohexyl bromide: MS (70 eV) m/z 164 (M +2), 162
+
(
M ), 83 (100%), 67, 55, 41.
–
1
benzyl bromide: IR (KBr) ν/cm 3086, 3063, 3030,
967, 2931, 2857, 1601, 1586, 1495, 1453, 1378, 1226,
201, 1098, 1068, 1028, 917, 812, 757, 694, 604, 547,
2
1
4
7
Supplementary Information
1
1
13
54. H NMR (CDCl , 200 MHz) δ 4.51 (s, 2H, CH Br),
H and C NMR, IR and MS spectra of
3
2
13
.27 – 7.44 (m, 5H, CHarom); C NMR (CDCl , 50 MHz)
synthesized compounds are available free of charge at
http://jbcs.sbq.org.br as PDF file.
3
δ 33.7 (CH Br), 128.5 (C ), 128.9 (C ), 129.2 (Carom),
2
arom
arom
+
+
1
37.9 (Carom); MS (70 eV) m/z 172 (M + 2), 170 (M ), 91
(
100%), 74, 65, 51.
Acknowledgment
–1
cinnamyl bromide: IR (KBr) ν/cm 3083, 3058, 3027,
959, 2924, 2852, 1644, 1596, 1576, 1495, 1449, 1430,
302, 1203, 1075, 970, 841, 748, 691, 622, 572, 493;
The authors thank CNPq and FAPERJ for the financial
support.
2
1
1
H NMR (CDCl , 200 MHz) δ 4.18 (d, 2H, J 7.8, CH ),
References
3
2
6
.41 (dt, 1H, J 15.6, 7.8, CH-CH Br), 6.67 (d, 1H, J 15.6,
2
1
3
PhCH), 7.27-7.43 (m, 5H, CHarom); C NMR (CDCl3,
1. Spargo, P. L.; Contemp. Org. Synth. 1994, 1, 113; Bohlmann, R.
In Comprehensive Organic Synthesis, vol. 6; Trost, B. M.;
Fleming, I., eds.; Pergamon Press: Oxford, UK, 1991.
2. Gribble, G. W.; Chem. Soc. Rev. 1999, 28, 335; Dembitsky,
V. M.; Russ. J. Bioorg. Chem. 2002, 28, 170; Gribble, G. W.;
Heterocycles 2012, 84, 157.
5
0 MHz) δ 33.6 (CH-Br), 125.4 (CH-CH Br), 126.9 (Carom),
2
128.5 (Carom), 128.8 (Carom), 134.7 (PhCH), 136.0 (Carom); MS
+
(
70 eV) m/z 117 (M - Br, 100%), 102, 91, 77, 63, 58, 51.
–
1
1
-bromo-2-ethylhexane: IR (KBr) ν/cm 2961,
2
1
2
929, 2873, 2859, 1458, 1436, 1379, 1267, 1253,
3. Firouzabadi, H.; Iranpoor, N.; Ebrahimzadeh, F.; Tetrahedron
Lett. 2006, 47, 1771.
1
226, 1099, 779, 765, 727, 650, 619. H NMR (CDCl ,
3
00 MHz) δ 0.85-0.92 (m, 6H, 2 CH ), 1.20-1.53 (m, 9H,
4. Vogel, A. I.; Cowan, D. M.; J. Chem. Soc. 1943, 636, 16.
5. Bridgewater, R. J.; Shoppee, C. W.; J. Chem. Soc. 1953, 1709;
Quallich, G. J.; Fox, D. E.; Friedmann, R. C.; Murtiashaw, C. W.;
J. Org. Chem. 1992, 57, 761; Sato, N.; Narita, N.; J. Heterocycl.
Chem. 1999, 36, 783.
3
1
3
CH -CH-(CH ) ), 3.45 (m, 2H, CH Br); C NMR (CDCl ,
5
2
2
2
3
2
3
0 MHz) δ 11.1 (CH ), 14.2 (CH ), 23.1 (C5), 25.4 (C4),
3
3
9.1 (CH -CH -CH), 32.1 (C3), 39.3 (C1), 41.3 (C2); MS
3
2
+
+
(
70 eV) m/z 165 (M + 2 - Et), 163 (M - Et), 137, 135,
8
3, 71, 57 (100%), 41.
6. Cason, J.; Correia, J. S.; J. Org. Chem. 1961, 26, 3645.
7
. Appel, R.; Angew. Chem. Int. Ed. 1975, 87, 801.
–
1
1
-bromo-4-methylpentane: IR (KBr) ν/cm 2958, 2935,
8. Matveeva, E. D.; Podrugina, T. A.; Zefirov, N. S.; Mendeleev
Commun. 1998, 8, 21.
2
871, 2852, 1468, 1438, 1386, 1368, 1299, 1254, 1208,