Continuous flow production of thermally unstable intermediates in a microreactor with inline IR-analysis: Controlled Vilsmeier-Haack formylation of electron-rich arenes

Organic Process Research and Development

Volumn 16, Issue 5, 2012, Pages 934-938

  Van Den Broek, Sebastiaan A M W ^a   Leliveld, Jeroen R ^b   Becker, René ^a   Delville, Mariëlle M E ^b   Nieuwland, Pieter J ^a   Koch, Kaspar ^a   Rutjes, Floris P J T ^b  

^a FutureChemistry Holding BV   (Netherlands)

^b RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CONTINUOUS FLOWS; ELECTRON-RICH ARENES; FINE CHEMICALS; FLOW CHEMISTRY; FORMYLATION; HAZARDOUS CHEMICALS; IN-LINE; INDUSTRIAL-SCALE PRODUCTION; INTRINSICALLY SAFE; MICRO-REACTOR; ORGANIC SYNTHESIS; PHARMACEUTICAL PRODUCTS; REACTIVE INTERMEDIATE; SCALE-UP; SEMI-AUTOMATED; THERMALLY UNSTABLE;

ALDEHYDES;

IONIC LIQUIDS;

EID: 84862080733     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op2003437     Document Type: Article

References (30)

1. Gattermann, L.; Koch, J. A. Ber. 1897, 30, 1622-1624
2. Vilsmeier, A.; Haack, A. Ber. 1927, 60, 119-122
3. Rahm, A.; Guilhemat, R.; Pereyre, M. Synth. Commun. 1982, 12, 485-487
4. Duff, J. C.; Bills, E. J. J. Chem. Soc. 1932, 1987-1988
5. Reimer, K.; Tiemann, F. Ber. 1876, 9, 824-828
6. Rieche, A.; Gross, H.; Hoft, E. Chem. Ber. 1960, 91, 88-91
7. Bollyn, M. Org. Process Res. Dev. 2005, 9, 982-996
8. Meth-Cohn, O.; Stanforth, S. P. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 777-794.
9. Lai, G.; Xiu, R.; Santos, J.; Mintz, E. A. Synlett 1997, 1275-1278
10. Perumal, P. T.; Amaresh, R. R. Tetrahedron 1999, 55, 8083-8094
11. Pedras, M. S. C.; Zaharia, I. L. Org. Lett. 2001, 3, 1213-1216
12. Marson, C. M.; Giles, P. R. Synthesis Using Vilsmeier Reagents; CRC: Boca Raton, 1994.
13. Marson, C. M. Tetrahedron 1992, 48, 3659-3726
14. Fujisawa, T.; Lida, S.; Sato, T. Chem. Lett. 1984, 1173-1176
15. Newman, M. S.; Sujeeth, P. K. J. Org. Chem. 1978, 43, 4367-4369
16. Boeckman, R. K., Jr.; Ganem, B. Tetrahedron Lett. 1974, 15, 913-917
17. Majo, V. J.; Perumal, P. T. Tetrahedron Lett. 1997, 38, 6889-6892
18. Rao, M. S. C.; Rao, G. S. K. Indian J. Chem., Sec. B. 1988, 27, 213-216
19. Jugie, G.; Smith, J. A. S.; Martin, G. J. J. Chem. Soc., Perkin Trans. 2 1975, 925-928
20. Dyer, U. C.; Henderson, D. A.; Mitchell, M. B.; Tiffin, P. D. Org. Process Res. Dev. 2002, 6, 311-316
21. Min, K.; Lee, T.-H.; Park, C. P.; Wu, Z.-Y.; Girault, H. H.; Ryu, I.; Fukuyama, T.; Mukai, Y.; Kim, D. Angew. Chem., Int. Ed. 2010, 49, 7063-7067. Unfortunately, this article does not describe any process details
22. Noland, W. E.; Lanzatella, N. P.; Sizova, E. P.; Venkatraman, L.; Afanasyev, O. V. J. Heterocycl. Chem. 2009, 46, 503-534
23. MacInnes, J. M.; Vikhansky, A.; Allen, R. W. K. Chem. Eng. Sci. 2007, 62, 2718-2727
24. For more detailed information on the FlowIR, see www.mt.com/FlowIR.
25. For information on the FlowStart Evo, see www.futurechemistry.com.
26. Nieuwland, P. J.; Segers, R.; Koch, K.; van Hest, J. C. M.; Rutjes, F. P. J. T. Org. Process Res. Dev. 2011, 15, 783-787
27. Nieuwland, P. J.; Koch, K.; van Harskamp, N.; Wehrens, R.; van Hest, J. C. M.; Rutjes, F. P. J. T. Chem. Asian J. 2010, 10, 799-805
28. Delville, M. M. E.; Nieuwland, P. J.; Janssen, P.; Koch, K.; van Hest, J. C. M.; Rutjes, F. P. J. T. Chem. Eng. J. 2010, 167, 556-559
29. 1H NMR data are in agreement with literature: Choy, J.; Jaime-Figueroa, S.; Jiang, L.; Wagner, P. Synth. Commun. 2008, 38, 3840-3853
30. Nieuwland, P. J.; Koch, K.; van Hest, J. C. M.; Rutjes, F. P. J. T. Open Chem. Eng. J. 2010, 4, 61-67