Zhang et al.
NOTE
Benzoic acid m.p. 125—127 ℃ (lit.17 124—126
(c) Wilgus, C. P.; Downing, S.; Molitor, E.; Bains, S.; Pagni,
R. M.; Kabalka, G. W. Tetrahedron Lett. 1995, 36, 3469.
(d) Sponholtz III, W. R.; Pagni, R. M.; Kabalka, G. W.;
Green, J. F.; Tan, L. C. J. Org. Chem. 1991, 56, 5700.
(a) Kabalka, G. W.; Pagni, R. M.; Hair, C. M. Org. Lett.
1999, 1, 1423.
(b) Kabalka, G. W.; Pagni, R. M.; Wang, L.; Namboodiri,
V.; Hair, C. W. Green Chem. 2000, 2, 120.
(c) Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M.
Tetrahedron Lett. 2000, 41, 5151.
℃). 1H NMR (DMSO-d6, 400 MHz) δ: 8.15—8.12 (m,
2H), 7.63—7.60 (m, 1H), 7.50—7.46 (m, 2H); 13C
NMR (DMSO-d6, 100 MHz) δ: 172.67, 133.84, 130.19,
129.24, 128.46.
5
p-Methoxybenzoic acid m.p. 182—184 ℃ (lit.18
184—185 ℃). 1H NMR (DMSO-d6, 400 MHz) δ: 8.07
(d, J=8.0 Hz, 2H), 6.95 (d, J=8.0 Hz, 2H), 3.89 (s,
3H); 13C NMR (DMSO-d6, 100 MHz) δ: 167.31, 162.69,
132.34, 123.46, 113.71, 55.48.
p-Bromobenzoic acid m.p. 248—250 ℃ (lit.19
(d) Kabalka, G. W.; Wang, L.; Pagni, R. M. Synlett 2001,
108.
1
250—252 ℃). H NMR (DMSO-d6, 400 MHz) δ: 7.87
(d, J=8.4 Hz, 2H), 7.62 (d, J=8.0 Hz, 2H); 13C NMR
(DMSO-d6, 100 MHz) δ: 166.77, 131.12, 130.77, 129.23,
126.92.
6
(a) Abramovich, R. A. Org. Prep. Proced. Int. 1991, 23, 683.
(b) Blettner, C. G.; Koenig, W. A.; Wilfried, A.; Stenzel, W.;
Schotten, T. J. Org. Chem. 1999, 64, 3885.
(c) Bose, D. S.; Jayalakshmi, B. J. Org. Chem. 1999, 64,
1713.
(d) Majetich, G.; Wheless, K. In Microwave-Enhanced
Chemistry, Eds.: Kingston, H. M.; Haswell, S. J., American
Chemical Society, Washington, D. C., 1997, pp. 455—505.
(e) Varma, R. S.; Namboodiri, V. V. Chem. Commun. 2001,
643.
Kajigaeshi, S.; Asano, K.; Fujisaki, S.; Kakinami, T.; Oka-
moto, T. Chem. Lett. 1989, 463.
Pasha, M. A.; Jayashankara, V. P. J. Chem. Res., Synop.
2004, 282.
Akabori, S.; Takanohashi, Y. J. Chem. Soc., Perkin Trans. 1
1991, 479.
p-Nitrobenzoic acid m.p. 122 —124 ℃ (lit.20
120—122 ℃). 1H NMR (DMSO-d6, 400 MHz) δ: 8.31 (d,
J=8.0 Hz, 2H), 8.15 (d, J=8.0 Hz, 2H); 13C NMR
(DMSO-d6, 100 MHz) δ: 165.77, 149.75, 136.54, 130.73,
123.31.
Conclusions
7
8
9
A reliable, rapid and practical procedure for the de-
protection of amides has been developed which involves
the use of a solvent-free mixture of potassium fluoride
doped alumina under microwave irradiation. The reac-
tion is environmentally friendly and results in excellent
yields of desired products.
10 Bradley, D. C.; Thomas, I. M. J. Chem. Soc. 1960, 3857.
11 Harland, P. A.; Hodge, P.; Maughan, W.; Wildsmith, E.
Synthesis 1984, 941.
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