A general, convenient and highly efficient synthesis of diarylmethanes by copper-catalyzed reaction

Tetrahedron Letters

Volumn 37, Issue 12, 1996, Pages 1949-1952

  Ku, Yi Yin ^a   Patel, Ramesh R ^a   Sawick, David P ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL DERIVATIVE; DIPHENYLMETHANE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029925161     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00176-1     Document Type: Article

References (17)

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2. Summers, J. B.; Gunn, B. P.; and Brooks, D. W. US Patent 4,873,259, Oct 10, 1989.
3. Samuelesson, B. Science, 1983, 120, 568.
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5. Brooks, D. W.; Stewart, A. O.; Basha, A.; Bhatia, P. A.; and Ratajczyk, J. D. US patent 5,288,751, Feb. 22, 1994.
6. a) Jakobsen, H. J.; Larsen, E. H.; Lawesson, S. O. Tetrahedron 1963, 19, 1867.
7. b) Ramanathan, V.; Levine, R. J. Org. Chem. 1962, 27, 1667.
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9. a) Olah, G. A. Acc. Chem. Res. 1971, 4, 240,
10. b) Olah, G. A.; Kobayashi, S.; Tashiro, M. J. Am. Chem. Soc. 1972, 94 7448.
11. Jaouhari, R. and Dixneuf, P. H. Inorg. Chim. Acta. 1988, 145, 179
12. Tamura, M.; Kochi, J. Synthesis 1971, 303.
13. Negishi, E.; King, A. O.; Okukado, N. J. Org. Chem. 1977, 42, 1821.
14. For an extensive review on the cross-coupling reaction with organocuprates, see Posner, G. H. Org. React. 1975, 22, 253.
15. Preparation of 4-fluorobenzyl iodide: A mixture of 4-fluorobenzyl chloride (14.46 g, 0.1 mol) and NaI (18.0 g, 0.12 mol) in THF (50 ml) was heated to 65°C ∼ 70°C for 3 h (GC-MS showed that all the 4-fluorobenzyl chloride was converted to the 4-fluorobenzyl iodide). The mixture was cooled to room temperature and was used in the next step directly.
16. The solution was prepared by mixing lithium chloride (0.85 g, 20 mmol) and copper chloride (1.35 g, 10 mmol) in THF (100 ml) at R.T.
17. 4Cl solution (100 ml), the mixture was stirred for 30 min., the organic layer was separated and washed with 10% sodium thiosulfate solution (50 ml), followed by distilled water (100 ml). The organic layer was then dried over MgSO4 and concentrated to give 19 g of 2-(4-fluorobenzyl)thiophene as an oil. Purification can be achieved by vacuum distillation (110°C, 5mmHg).