First general, direct, and regioselective synthesis of substituted methoxybenzoic acids by ortho metalation

Journal of Organic Chemistry

Volumn 72, Issue 9, 2007, Pages 3419-3429

  Nguyen, Thi Huu ^a   Chau, Nguyet Trang Thanh ^a,b   Castanet, Anne Sophie ^a   Nguyen, Kim Phi Phung ^b   Mortier, Jacques ^a  

^a UNIVERSITÉ DU MAINE   (France)

^b Laboratoire de Chimie Organique   (Viet Nam)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC CHEMISTRY; CARBOXYLATE; METALATION; METHOXYBENZOIC ACIDS;

REACTION KINETICS; REGIOSELECTIVITY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CARBOXYLIC ACIDS;

ANISIC ACID; AROMATIC COMPOUND; BENZOIC ACID DERIVATIVE; BUTANE; CARBOXYLIC ACID; LITHIUM 2,2,6,6 TETRAMETHYLPIPERIDIDE; LITHIUM DERIVATIVE; METAL; METHOXYBENZOIC ACID DERIVATIVE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; METALLATION; ORGANIC CHEMISTRY; ORTHO METALLATION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 34247636039     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070082a     Document Type: Article

References (94)

1. Reviews: (a) Snieckus, V. Chem. Rev. 1990, 90, 879.
2. (b) Hartung, C. G.; Snieckus, V. Modern Arene Chemistry; Astruc, D. Ed.; Wiley-VCH: New York; 2002, p. 330.
3. (c) Schlosser, M. Angew. Chem., Int. Ed. 2005, 44, 376.
4. Beak, P.; Brown, R. A. J. Org. Chem. 1977, 42, 1823.
5. Comins, D. L.; Brown, J. D. J. Org. Chem. 1986, 51, 3566.
6. Reitz, D. B.; Massey, S. M. J. Org. Chem. 1990, 55, 1375.
7. Snieckus, V. Lect. Heterocycl. Chem. 1984, 95.
8. Puterbaugh, W. H.; Hauser, C. R. J. Org. Chem. 1964, 29, 853.
9. Narasimhan, N. S.; Bhide, B. H. Tetrahedron 1971, 27, 6171.
10. See also: Fisher, L. E.; Muchowski, J. M.; Clark, R. D. J. Org. Chem. 1992, 57, 2700.
11. (a) Gohier, F.; Castanet, A.-S.; Mortier, J. Org. Lett. 2003, 5, 1919.
12. (b) Gohier, F.; Mortier, J. J. Org. Chem. 2003, 68, 2030.
13. (c) Tilly, D.; Samanta, S. S.; De, A.; Castanet, A.-S.; Mortier, J. Org. Lett. 2005, 7, 827.
14. (d) Tilly, D.; Castanet, A.-S.; Mortier, J. Chem. Lett. 2005, 34, 446.
15. (e) Gohier, F.; Castanet, A.-S.; Mortier, J. J. Org. Chem. 2005, 70, 1501.
16. Conjugate addition of organolithium reagents to unprotected 1- and 2-naphthalenecarboxylic acids (a) Plunian, B.; Mortier, J.; Vaultier, M.; Toupet, L. J. Org. Chem. 1996, 61, 5206.
17. (b) Plunian, B.; Vaultier, M.; Mortier, J. J. Chem. Soc. Chem. Commun. 1998, 81. Nucleophilic aromatic substitutions of 2-fluorobenzoic acid with organolithiums: see ref. 9a.
18. Mongin, F.; Maggi, R.; Schlosser, M. Chimia 1996, 50, 650.
19. Beak, P.; Brown, R. A. J. Org. Chem. 1982, 47, 34.
20. Preliminary report: Nguyen, T. H.; Castanet, A.-S.; Mortier, J. Org. Lett. 2006, 8, 765.
21. (a) Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356.
22. (b) Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206.
23. (a) Van Eikema Hommes, N. J. R.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1992, 31, 755.
24. (b) Bauer, W.; Schleyer, P. v. R. J. Am. Chem. Soc. 1989, 111, 7191.
25. (c) Van Eikema Hommes, N. J. R.; Schleyer, P. v. R. Tetrahedron 1994, 50, 5903.
26. Nguyen, T. H.; Chau, N. T. T.; Castanet, A.-S.; Nguyen, K. P. P.; Mortier, J. Org. Lett. 2005, 7, 2445.
27. Olofson, R. A.; Dougherty, C. M. J. Am. Chem. Soc. 1973, 95, 581.
28. Reviews: (a) Lochmann, L. Eur. J. Inorg. Chem. 2000, 1115.
29. (b) Schlosser, M. Eur. J. Org. Chem. 2001, 3975.
30. Quirck, R. P.; Kester, D. E. J. Organomet. Chem. 1974, 72, C23.
31. Attempts of crystallization for X-ray structure determination in ether or THF failed.
32. 2Li prepared by slow addition of 2 mol of n-BuLi to 2-bromobenzoic acid is allowed to warm up to -20°C and to remain at the temperature for 5 h, acidification affords the self-condensation product 2-benzoylbenzoic acid in 68% yield. Parham, W. E.; Bradsher, C. K.; Edgar, K. J. J. Org. Chem. 1981, 46, 1057.
33. (b) The same dianion generated by metalation of benzoic acid with s-BuLi/TMEDA at -90°C degrades above -20°C: Bennetau, B.; Mortier, J.; Moyroud, J.; Guesnet, J.-L. J. Chem Soc. Perkin Trans. 1 1995, 1265.
34. See, inter alia: (a) Bender, C. L.; Rangaswamy, V.; Loper, J. Annu. Rev. Phytopathol. 1999, 37, 175.
35. (b) Tyman, J. H. P. Recent Res. Dev. Lipids 2001, 5, 125.
36. (c) Katz, L. Chem. Rev. 1997, 97, 2557.
37. (d) Staunton, J.; Weissman, K. J. Nat. Prod. Rep. 2001, 18, 380.
38. Selected examples of uses of 2-methoxy-6-methylbenzoic acid (4a) as a building block for natural product synthesis: (e) Kotsuki, H.; Araki, T.; Miyazaki, A.; Iwasaki, M.; Datta, P. K. Org. Lett. 1999, 1, 499.
39. (f) Ghosh, A. K.; Bischoff, A.; Cappiello, J. Org. Lett. 2001, 3, 2677.
40. 2-Bromo-6-methoxybenzoic acid (4d): (g) Sugaya, T.; Mimura, Y.; Kato, N.; Ikuta, M.; Mimura, T.; Kasai, M.; Tomioka, S. Synthesis 1994, 73.
41. (h) Mimura, Y.; Shida, Y.; Kasai, M.; Ashizawa, T.; Gomi, K. European Patent EP0487097A1, 1992.
42. 2-Iodo-6-methoxybenzoic acid (4e) (i) Martin, N. M. B.; Smith, G. C. M.; White, C. R.; Newton, R. F.; Douglas, D. G.; Eversley, P. J.; Vile, J. World Patent WO 0236576 A1, 2002.
43. Selected examples of uses of 3-methoxy-4-methylbenzoic acid (7a) as a building block for natural product synthesis: (a) Eickhoff, J. E.; Hafenbradl, D.; Schwab, W.; Cotton, M.; Klebl, B. M.; Zech, B.; Müller, S.; Harris, J.; Savic, V.; Macritchie, J.; Sherborne, B.; Le, J. PCT Int. Appl WO 010637, 1996.
44. (b) Majetich, G.; Hicks, R.; Zhang, Y.; Tian, X.; Feltman, T. L.; Fang, J.; Duncan, S., Jr. J. Org. Chem. 1996, 61, 8169.
45. (c) Raju, B. G.; Odowd, H.; Gao, H.; Patel, D. V.; Trias, J. PCT Int. Appl. WO 2004 007444, 2004.
46. (d) Gauuan, P. J. F.; Trova, M. P.; Gregor-Boros, L.; Bocckino, S. B.; Crapo, J. D.; Day, B. J. Bioorg. Med. Chem. 2002, 10, 3013.
47. 2-Chloro-4-methoxybenzoic acid (9c): (e) Pellon Comdom, R. F.; Docampo Palacios, M. L. Synth. Commun. 2003, 33, 921.
48. 2-Bromo-4-methoxybenzoic acid (9d): (f) Bamford, M. J.; Heightman, T. D.; Wilson, D. M.; Witherington, J. PCT Int. Appl. WO 2005 087746, 2005.
49. (g) Croisy-Delcey, M.; Croisy, A.; Carrez, D.; Huel, C.; Chiaroni, A.; Ducrot, P.; Bisagni, E.; Jin, L.; Leclercq, G. Bioorg. Med. Chem. 2000, 8, 2629. 3-Hydroxy-7-methoxyisobenzofuran-1(3/7)-one (10).
50. (h) Haack, T.; Kurtkaya, S.; Snyder, J. P.; Georg. G. I. Org. Lett. 2003, 5, 5019.
51. See references in Table 1.
52. Weiss, U.; Edwards, J. M. The Biosynthesis of Aromatic Compounds Wiley: New York, 1980; Chapter 18.
53. Postmus, C., Jr.; Kaye, I. A.; Craig, C. A.; Matthews, R. S. J. Org. Chem. 1964, 29, 2693.
54. Lewis, A.; Stefanuti, I.; Swain, S. A.; Smith, S. A.; Taylor, R. J. K. Org. Biomol. Chem. 2003, 1, 104.
55. Cabiddu, S.; Melis, S.; Piras, P. P.; Secci, M. J. Organomet. Chem. 1977, 132, 321.
56. Freskos, J. N.; Morrow, G. W.; Swenton, J. S. J. Org. Chem. 1985, 50, 805.
57. Harland, P.; Hodge, P. Synthesis 1983, 419.
58. Yang, K. L.; Balckman, B.; Diedrich, W.; Flaherty, P. T.; Mossman, C. J.; Roy, S.; Ahn, Y. M.; Georg, G. I. J. Org. Chem. 2003, 68, 10030.
59. Letsinger, R. L.; Schnizer, A. W. J. Org. Chem. 1951, 16, 869.
60. 5d was prepared in many more steps than in this paper in (a) Farkas, L.; Sóti, F.; Incze, M.; Nógrádi, M. Chem. Ber. 1974, 107, 3874.
61. (b) Pudleiner, H.; Laatsch, H. Synthesis 1989, 286. (c) Sugaya, T.; Mimura, Y.; Kato, N.; Ikuta, M.; Mimura, T.; Kasai, M.; Tomioka, S. Synthesis 1994, 73.
62. Mortier, J.; Moyroud, J.; Bennetau, B.; Cain, P. J. Org. Chem. 1994, 59, 4042.
63. Huszthy, P.; Köntös, Z.; Vermes, B.; Pintér, A. Tetrahedron 2001, 23, 4967.
64. Stanley, W. M.; McMahon, E.; Roger, A. J. Am. Chem. Soc. 1933, 55, 706.
65. Brimble, M. A.; Caprio, V.; Johnston, A. D.; Sidford, M. Synthesis 2001, 855.
66. Nishioka, H.; Nagasawa, M.; Yoshida, K. Synthesis 2000, 243.
67. (a) Newman, M. S.; Bayerlein, F. J. Org. Chem. 1963, 28, 2804.
68. (b) Roberts, J. D.; Yancey, J. A. J. Am. Chem. Soc. 1951, 73, 1011.
69. Rauhut, M. M.; Bunnet, J. F. J. Org. Chem. 1956, 21, 939.
70. Merour, J.-Y.; Coadou, J.-Y.; Tatibouet, F. Synthesis 1982, 1053.
71. Wyrick, S. D.; Smith, F. T.; Kemp, W. E.; Grippo, A. A. J. Med. Chem. 1987, 30, 1798.
72. An expedient synthesis of lunularic acid, a growth inhibitor found in Lunularia cruciata was recently reported from 2-methoxy-6-methylbenzoic acid (4a) prepared according to this method. See ref 13.
73. Narashimhan, N. S.; Bhide, B. H. Tetrahedron 1971, 27, 6171.
74. Meyers, A. I.; Mihelich, E. D. J. Am. Chem. Soc. 1975, 97, 7383.
75. (a) Mills, R. J.; Taylor, N. J.; Snieckus, V. J. Org. Chem. 1989, 54, 4372.
76. (b) Sibi, M. P.; Miah, M. A. J.; Snieckus, V. J. Org. Chem. 1984, 49, 737.
77. (c) Watanabe, M.; Sahara, M.; Kubo, M.; Furukawa, S.; Billedeau, R. J.; Snieckus, V. J. Org. Chem. 1984, 49, 742.
78. Page, M. I. Angew. Chem., Int. Ed. Engl. 1977, 16, 449.
79. (a) Meyers, A. I.; Avila, W. B. Tetrahedron Lett. 1980, 21, 3335.
80. (b) Shimano, M.; Meyers, A. I. Tetrahedron Lett. 1997, 38, 5415.
81. Clark, R. D.; Jahangir, A. Org. React. 1995, 47, 1.
82. Mortier, J.; Vaultier, M.; Cantegril, R.; Dellis, P. Aldrichim. Acta 1997, 30, 34.
83. The base and Me3SiCl are premixed prior to addition of the acid. See: Krizan, T. D.; Martin, J. C. J. Am. Chem. Soc. 1983, 105, 6155.
84. (b) Schlosser, M.; Guio, L.; Leroux, F. J. Am. Chem. Soc. 2001, 123, 3822.
85. (c) Lipshutz, B. H.; Wood, M. R.; Lindsley, C. W. Tetrahedron Lett. 1995, 36, 4385.
86. Reviews: (a) Bunnett, J. F. Acc. Chem. Res. 1972, 5, 139.
87. (b) Queguiner, G.; Marsais, F.; Snieckus, V.; Epsztajn, J. Adv. Heterocycl. Chem. 1991, 52, 187. Recent examples: see ref 9a,b,e.
88. Under conditions B, the reaction leads to degradation products with DMF, allyl bromide, and benzyl bromide. Acid 2 also leads to degradation products by reaction with DMF under conditions D.
89. See Achmatowicz, O.; Szechne, B. J. Org. Chem. 2003, 68, 2398 and references cited therein.
90. Casas, R.; Cavé, C.; d'Angelo, J. Tetrahedron Lett. 1995, 36, 1039.
91. Parker, K. A.; Koziski, K. A. J. Org. Chem. 1987, 52, 674.
92. Schlosser, M. Organometallics in Synthesis. A Manual, 2nd ed.; Wiley: Chichester, 2002.
93. Koo, S.; Ki, E.-h.; Lee, K.-j. Synth. Commun. 2002, 32, 2275.
94. CAS number: 72856-74-7. Robertson, D. W.; Beedle, E. E.; Krushinski, J. H.; Don Pollock, G.; Wilson, H.; Wyss, V. L.; Hayes, J. S. J. Med. Chem. 1985, 28, 717. The melting point is not reported.