B.R. Kim et al. / Tetrahedron 69 (2013) 3234e3237
3237
(300 MHz, CDCl3)
d
2.46 (s, 3H), 7.36e7.39 (m, 3H), 7.50e7.52 (m,
(300 MHz, CDCl3)
d
1.28 (t, 3H, J1 and J2¼7.1 Hz), 4.33e4.40 (m, 2H),
2H). 13C NMR (75 MHz, DMSO-d6)
d
34.01, 126.42, 128.93, 129.46,
7.38e7.43 (m, 2H), 7.50e7.55 (m, 1H), 8.02e8.05 (m, 2H). 13C NMR
135.47, 196.42. HRMS (m/z): [M]þ calcd for C8H8OSe 199.9740.
Found: 199.9739.
(75 MHz, CDCl3) d 14.30, 60.89, 128.29, 129.51, 130.51, 132.77,
166.56. HRMS (m/z): [M]þ calcd for C9H10O2 150.0681. Found:
150.0685.
4.2.9. 4-Methoxyphenyl benzoate (6h). Yield: 360 mg, 98%. White
solid. Mp 84e85 ꢀC (lit.16 mp 85.5e86.5 ꢀC). IR (KBr, CH2Cl2) 3066,
2997, 2960, 2934, 2834, 1730, 1599, 1503, 1271, 1248, 1194, 1177,
4.2.15. Isopropyl benzoate (6n). Yield: 513 mg, 94%. Colorless oil. IR
(KBr, CH2Cl2) 3065, 2980, 2935, 1715, 1599, 1454, 1374, 1347, 1311,
1276, 1175, 1102, 1062, 1024, 919, 849, 711 cmꢁ1. 1H NMR (300 MHz,
1031, 869, 807 cmꢁ1
.
1H NMR (300 MHz, CDCl3)
d
3.81 (s, 3H),
6.91e6.96 (m, 3H), 7.10e7.15 (m, 2H), 7.47e7.64 (m, 3H), 8.17e8.20
(m, 2H). 13C NMR (75 MHz, CDCl3)
55.62, 114.55, 122.47, 128.56,
CDCl3)
d 1.35 (s, 3H), 1.37 (s, 3H), 5.21e5.29 (m, 1H), 7.38e7.43 (m,
d
2H), 7.49e7.54 (m, 1H), 8.02e8.06 (m, 2H). 13C NMR (75 MHz,
128.90, 129.68, 130.15, 130.59, 133.52, 144.45, 157.34, 165.55. HRMS
CDCl3) d 21.92, 68.28, 128.24, 129.49, 130.92, 132.67, 166.05. HRMS
(m/z): [M]þ calcd for C14H12O3 228.0786. Found: 228.0787.
(m/z): [M]þ calcd for C10H12O2 164.0837. Found: 164.0834.
4.2.10. 4-Methoxyphenyl 4-bromobenzoate (6i). Yield: 354 mg, 72%.
White solid. Mp 116e118 ꢀC (lit.17 mp 122e124 ꢀC). IR (KBr, CH2Cl2)
3096,2957, 2931, 2903, 2834, 1732, 1586, 1395, 1266, 1193, 1100,
Acknowledgements
This research was supported by the Basic Science Research
Program through the National Research Foundation of Korea (NRF)
funded by the Ministry of Education, Science and Technology
(2012R1A1A2001162).
1074, 1032, 872, 849, 816, 748 cmꢁ1 1H NMR (300 MHz, CDCl3)
.
d
3.81 (s, 3H), 6.90e6.96 (m, 2H), 7.08e7.14 (m, 2H), 7.61e7.66 (m,
2H), 8.02e8.06 (m, 2H). 13C NMR (75 MHz, CDCl3)
d
55.62, 114.57,
122.36, 128.58, 128.74, 131.63, 131.93, 144.23, 157.44, 164.85. HRMS
(m/z): [M]þ calcd for C14H11BrO3 305.9892. Found: 305.9893.
Supplementary data
4.2.11. 4-Methoxyphenyl 4-cyanobenzoate (6j). Yield: 360 mg, 88%.
Pale yellow solid. Mp 123e125 ꢀC. IR (KBr, CH2Cl2) 3072, 2965,
2912, 2841, 2228, 1742, 1601, 1504, 1292, 1256, 1195, 1071, 1017, 867,
Supplementary data associated with this article can be found in
819, 759, 681 cmꢁ1
.
1H NMR (300 MHz, CDCl3)
d
3.81 (s, 3H),
6.91e6.96 (m, 2H), 7.10e7.16 (m, 2H), 7.77e7.80 (m, 2H), 8.16e8.29
(m, 2H). 13C NMR (75 MHz, CDCl3)
55.63, 114.64, 116.90, 117.90,
References and notes
d
1. Kang, Y. J.; Chung, H.-A.; Kim, J. J.; Yoon, Y. J. Synthesis 2002, 733e738.
2. Kim, J. J.; Park, Y. D.; Kim, H. K.; Cho, S. D.; Kim, J. K.; Lee, S. G.; Yoon, Y. J. Synth.
Commun. 2005, 35, 731e738.
3. Kim, J. J.; Park, Y. D.; Cho, S. D.; Kim, H. K.; Kang, Y. J.; Lee, S. G.; Falck, J. R.; Shiro,
M.; Yoon, Y. J. Bull. Korean Chem. Soc. 2004, 25, 1273e1276.
4. Park, Y. D.; Kim, J. J.; Chung, H.-A.; Kweon, D. H.; Cho, S. D.; Lee, S. G.; Yoon, Y. J.
Synthesis 2003, 560e564.
5. Smith, M. B.; March, J. March’s Advanced Organic Chemistry, 5th ed.; Wiley
Interscience: New York, NY, 2001.
6. Lee, H. G.; Kim, M. J.; Park, S. E.; Kim, J. J.; Kim, B. R.; Lee, S. G.; Yoon, Y. J. Synlett
2009, 2809e2814.
7. Kim, S. K.; Kweon, D. H.; Cho, S. D.; Kang, Y. J.; Park, K. H.; Lee, S. G.; Yoon, Y. J.
J. Heterocycl. Chem. 2005, 42, 353e359.
8. Sung, G. H.; Kim, B. R.; Lee, S. G.; Kim, J. J.; Yoon, Y. J. Curr. Org. Chem. 2012, 16,
852e858.
9. Kim, B. R.; Lee, H. G.; Kim, E. J.; Lee, S. G.; Yoon, Y. J. J. Org. Chem. 2010, 75,
484e486.
122.22, 130.59, 132.38, 133.50, 144.01, 157.62, 163.93. HRMS (m/z):
[M]þ calcd for C15H11NO3 253.0739. Found: 253.0737.
4.2.12. 4-Methoxyphenyl 4-methoxybenzoate (6k). Yield: 410 mg,
98%. White solid. Mp 123e124 ꢀC (lit.18 mp 123e123.5 ꢀC). IR (KBr,
CH2Cl2) 3016, 2964, 2933, 2907, 2837, 1721, 1604, 1510, 1453, 1319,
1274, 1248, 1193, 1163, 1071, 1023, 867, 843, 812, 787, 761, 743 cmꢁ1
.
1H NMR (300 MHz, CDCl3)
d 3.80 (s, 3H), 3.86 (s, 3H), 6.90e6.97 (m,
4H), 7.08e7.12 (m, 2H), 8.13 (d, 2H, J¼8.5 Hz). 13C NMR (75 MHz,
DMSO-d6)
d
55.50, 55.61, 113.82, 114.49, 121.97, 122.55, 132.25,
144.56, 157.23, 163.85, 165.27. HRMS (m/z): [M]þ calcd for C15H14O4
258.0892. Found: 258.0890.
10. Won, J. E.; Kim, H. K.; Kim, J. J.; Yim, H. S.; Kim, M. J.; Kang, S. B.; Chung, H.-A.;
Lee, S. G.; Yoon, Y. J. Tetrahedron 2007, 63, 12720e12730.
11. Hwang, J.; Hwang, Y.; Yang, K.; Yoon, Y. J.; Koo, I. S. Bull. Korean Chem. Soc. 2009,
30, 2779e2781.
12. Further works on the kinetics between solid reaction and solution reaction
under our conditions are under way by other groups. The results will be
published elsewhere.
13. Magens, S.; Ertelt, M.; Jatsch, A.; Plietker, B. Org. Lett. 2008, 10, 53e56.
14. Mþ of 6b do not detect in mass spectra, but the mass spectra of 6b show
the same pattern in the literature: Zubarovskii, V. M.; Verbovskaya, T. M.;
Kiprianov, A. I. Russ. J. Gen. Chem. 1961, 31, 3056e3062.
15. Usha, G.; Deshanie, G.; Viswajanani, J. S.; Kathryn, E. C.; Deborah, J. M.;
Benita, S. K.; John, A. K. Bioorg. Med. Chem. 2003, 11, 629e657.
16. Petersen, T. B.; Khan, R.; Olofsson, B. Org. Lett. 2011, 13, 3462e3465.
17. Petricci, E.; Mugnaini, C.; Radi, M.; Corelli, F.; Botta, M. J. Org. Chem. 2004, 69,
7880e7887.
4.2.13. 4-Methoxyphenyl heptanoate (6l). Yield: 378 mg, 99%. Col-
orless oil. IR (KBr, CH2Cl2) 2954, 2930, 2857, 1755, 1504, 1463, 1373,
1248, 1194, 1142, 1101, 1033, 839, 749, 518 cmꢁ1. 1H NMR (300 MHz,
CDCl3)
d
0.89 (t, 3H, J1¼6.7 Hz, J2¼6.6 Hz), 1.28e1.43 (m, 6H),
1.66e1.76 (m, 2H), 2.49 (t, 2H, J1¼7.5 Hz, J2¼7.4 Hz), 3.72 (s, 3H),
6.82e6.87 (m, 2H), 6.94e6.99 (m, 2H). 13C NMR (75 MHz, CDCl3)
d
14.03, 22.52, 24.94, 28.80, 31.48, 34.30, 55.44, 114.38, 122.32,
144.32, 157.19, 172.56. HRMS (m/z): [M]þ calcd for C14H20O3
236.1412. Found: 236.1411.
4.2.14. Ethyl benzoate (6m). Yield: 601 mg, 92%. Colorless oil. IR
(KBr, CH2Cl2) 3064, 3032, 2982, 2936, 2903, 1717, 1599, 1450, 1391,
18. Arisawa, M.; Igarashi, Y.; Kobayashi, H.; Yamada, T.; Bando, K.; Ichikawa, T.;
Yamaguchi, M. Tetrahedron 2011, 67, 7846e7859.
1366, 1308, 1272, 1171, 1107, 1069, 1024, 871, 849 cmꢁ1 1H NMR
.