The continuous flow synthesis of 2,4,5-trifluorobenzoic acid via sequential Grignard exchange and carboxylation reactions using microreactors

Chemical Engineering Journal

Volumn 262, Issue , 2015, Pages 1168-1174

  Deng, Qiulin ^a   Shen, Ruwei ^a   Zhao, Zhimin ^a   Yan, Meimei ^a   Zhang, Lixiong ^a  

^a NANJING TECH UNIVERSITY   (China)

Author keywords

2,4,5 Trifluorobenzoic acid; Carbon dioxide; Gas liquid reaction; Grignard exchange; Microflow

Indexed keywords

CARBON DIOXIDE; CARBOXYLATION; CHEMICAL REACTORS; LIQUIDS; MIXERS (MACHINERY); SYNTHESIS (CHEMICAL); TUBES (COMPONENTS);

CONTINUOUS-FLOW SYNTHESIS; ETHYLMAGNESIUM BROMIDE; GAS-LIQUID REACTION; GRIGNARD; MICRO-FLOW; PHARMACEUTICAL INDUSTRY; REACTION PARAMETERS; SYNTHETIC INTERMEDIATES;

CHEMICAL REACTIONS;

EID: 84910008117     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2014.10.066     Document Type: Article

References (52)

1. Hiyama T., Kanie K., Kusumoto T., Morizawa Y., Shimizu M. Organofluorine Compounds: Chemistry and Application 2000, Springer-Verlag, Berlin.
2. Kirsch P. Modern Fluoroorganic Chemistry 2004, Wiley-VCH, Weinheim.
3. Uneyama K. Organofluorine Chemistry 2006, Blackwell, Oxford.
4. Tran T.P., Ellsworth E.L., Sanchez J.P., Watson B.M., Stier M.A., Showalter H.D.H., Domagala J.M., Shapiro M.A., Joannides E.T., Gracheck S.J., Nguyen D.Q., Bird P., Yip J., Sharadendu A., Ha C., Ramezani S., Wu X., Singh R. Structure-activity relationships of 3-aminoquinazolinediones, a new class of bacterial type-2 topoisomerase (DNA gyrase and topo IV) inhibitors. Bioorg. Med. Chem. Lett. 2007, 17:1312-1320.
5. Tran T.P., Ellsworth E.L., Stier M.A., Domagala J.M., Showalter H.D.H., Gracheck S.J., Shapiro M.A., Joannides T.E., Singh R. Synthesis and structural-activity relationships of 3-hydroxyquinazoline-2,4-dione antibacterial agents. Bioorg. Med. Chem. Lett. 2004, 14:4405-4409.
6. Sanchez J.P., Domagala J.M., Hagen S.E., Heifetz C.L., Hutt M.P., Nichols J.B., Trehan A.K. Quinolone antibacterial agents. Synthesis and structure-activity relationships of 8-substituted quinoline-3-carboxylic acids and 1,8-naphthyridine-3-carboxylic acids. J. Med. Chem. 1988, 31:983-991.
7. Chu D.T.W., Nordeen C.W., Hardy D.J., Swanson R.N., Giardina W.J., Pernet A.G., Plattner J.J. Synthesis, antibacterial activities, and pharmacological properties of enantiomers of temafloxacin hydrochloride. J. Med. Chem. 1991, 34:168-174.
8. Barnes D.M., Christesen A.C., Engstrom K.M., Haight A.R., Hsu M.C., Lee E.C., Peterson M.J., Plata D.J., Raje P.S., Stoner E.J., Tedrow J.S., Wagaw S. Chlorination at the 8-position of a functionalized quinolone and the synthesis of quinolone antibiotic ABT-492. Org. Process Res. Dev. 2006, 10:803-807.
9. Renau T.E., Sanchez J.P., Shapiro M.A., Dever J.A., Gracheck S.J., Domagala J.M. Effect of lipophilicity at N-1 on activity of fluoroquinolones against Mycobacteria. J. Med. Chem. 1995, 38:2974-2977.
10. Anquetin G., Greiner J., Vierling P. Synthesis of mono- and di-substituted 2,4,5-trifluorobenzoic acid synthons, key precursors for biologically active 6-fluoroquinolones. Tetrahedron 2005, 61:8394-8404.
11. Beylin V., Boyles D.C., Curran T.T., Macikenas D., Parlett R.V., Vrieze D. The preparation of two, preclinical amino-quinazolinediones as antibacterial agents. Org. Process Res. Dev. 2007, 11:441-449.
12. Gomez C., Ponien P., Serradji N., Lamouri A., Pantel A., Capton E., Jarlier V., Anquetin G., Aubry A. Synthesis of gatifloxacin derivatives and their biological activities against Mycobacterium leprae and Mycobacterium tuberculosis. Bioorg. Med. Chem. 2013, 21:948-956.
13. Rainbolt J.E., Koech P.K., Polikarpov E., Swensen J.S., Cosimbescu L., Ruden A.V., Wang L., Sapochak L.S., Padmaperuma A.B., Gaspar D.J. Synthesis and characterization of p-type conductivity dopant 2-(3-(adamantan-1-yl)propyl)-3,5,6-trifluoro-7,7,8,8-tetracyanoquin-odimethane. J. Mater. Chem. C 2013, 1:1876-1884.
14. Belf L.J., Buxton M.W., Tilney-Bussett J.F. Some reactions of 1,2,3,4-tetrafluoro-benzene and derived compounds. Tetrahedron 1967, 23:4719-4727.
15. O'Reilly N.J., Derwin W.S., Fertel L.B., Lin H.C. An expedient route to the quinolone antibacterial intermediate, 2,4,5-triouorobenzoic acid. Synlett 1990, 609-610.
16. Fertel L.B. Process improvements in the synthesis of 2,4,5-trifluorobenzoic acid. Selective hydrodefluorination of tetrafluorophthalimides. Org. Process Res. Dev. 1998, 2:111-115.
17. Mutule I., Suna E. Arylzinc species by microwave assisted Grignard formation-transmetallation sequence: application in the Negishi coupling. Tetrahedron 2005, 61:11168-11176.
18. Micro Reaction Technology in Organic Synthesis 2011, CRC Press, Boca Raton. C. Wiles, P. Watts (Eds.).
19. Watts P., Haswell S.J. The application of micro reactors for organic synthesis. Chem. Soc. Rev. 2005, 34:235-246.
20. Taghavi-Moghadam S., Kleemann A., Golbig K.G. Microreaction technology as a novel approach to drug design, process development and reliability. Org. Process Res. Dev. 2001, 5:652-658.
21. Haswell S.J., Middleton R.J., O'Sullivan B., Skelton V., Watts P., Styring P. The application of micro reactors to synthetic chemistry. Chem. Commun. 2001, 391-398.
22. Bellefon C., Tanchoux N., Caravieilhes S., Grenouillet P., Hessel V. Microreactors for dynamic, high throughput screening of fluid/liquid molecular catalysis. Angew. Chem., Int. Ed. 2000, 39:3442-3445.
23. Jähnisch K., Hessel V., Löwe H., Baerns M. Chemistry in microstructured reactors. Angew. Chem., Int. Ed. 2004, 43:406-446.
24. Lau W.N., Yeung K.L., Martin-Arand R. Knoevenagel condensation reaction between benzaldehyde and ethyl acetoacetate in microreactor and membrane microreactor. Microporous Mesoporous Mater. 2008, 115:156-163.
25. Yeung K.L., Kwan S.M., Lau W.N. Zeolites in microsystems for chemical synthesis and energy generation. Top Catal. 2009, 52:101-110.
26. Jensen K.F., Reizman B.J., Newman S.G. Tools for chemical synthesis in microsystems. Lab Chip 2014, 14:3206-3212.
27. Noël T., Buchwald S.L. Cross-coupling in flow. Chem. Soc. Rev. 2011, 40:5010-5029.
28. Sharma S., Maurya R.A., Min K.I., Jeong G.Y., Kim D.P. Odorless isocyanide chemistry: an integrated microfluidic system for a multistep reaction sequence. Angew. Chem., Int. Ed. 2013, 52:7564-7568.
29. Jahnisch K., Baerns M., Hessel V., Ehrfeld W., Haverkamp V., Löwe H., Wille C., Guber A. Direct fluorination of toluene using elemental fluorine in gas/liquid microreactors. J. Fluorine Chem. 2000, 105:117-128.
30. Kawaguchi T., Miyata H., Ataka K., Mae K., Yoshida J. Room-temperature swern oxidations by using a microscale flow system. Angew. Chem., Int. Ed. 2005, 44:2413-2416.
31. 2 in a tube-in-tube gas permeable membrane reactor. Angew. Chem., Int. Ed. 2011, 50:1190-1193.
32. Vaccaro L., Lanari D., Marrocchi A., Strappaveccia G. Flow approaches towards sustainability. Green Chem. 2014, 16:3680-3704.
33. van den Broek S.A.M.W., Leliveld J.R., Becker R., Delville M.M.E., Nieuwland P.J., Koch K., Rutjes F.P.J.T. Continuous flow production of thermally unstable intermediates in a microreactor with inline ir-analysis: controlled Vilsmeier-Haack formylation of electron-rich arenes. Org. Process Res. Dev. 2012, 16:934-938.
34. Mawatari K., Kazoe Y., Aota A., Tsukahara T., Sato K., Kitamori T. Microflow systems for chemical synthesis and analysis: approaches to full integration of chemical process. J. Flow Chem. 2012, 1:3-12.
35. Hessel V., Kralisch D., Kockmann N., Noël T., Wang Q. Novel process windows for enabling, accelerating, and uplifting flow chemistry. ChemSusChem 2013, 6:746-789.
36. Noël T., Hessel V. Membrane microreactors: gas-liquid reactions made easy. ChemSusChem 2013, 6:405-407.
37. Sobieszuk P., Aubin J., Pohorecki R. Hydrodynamics and mass transfer in gas-liquid flows in microreactors. Chem. Eng. Technol. 2012, 35:1346-1358.
38. Günther A., Jensen K.F. Multiphase microfluidics: from flow characteristics to chemical and materials synthesis. Lab Chip 2006, 6:1487-1503.
39. Deng Q., Shen R., Ding R., Zhang L. Generation of ethynyl-Grignard reagent in a falling film microreactor: an expeditious flow synthesis of propargylic alcohols and analogues. Adv. Synth. Catal. 2014, 356:2931-2936.
40. Yu Z., Lv Y., Yu C. A continuous kilogram-scale process for the manufacture of o-difluorobenzene. Org. Process Res. Dev. 2012, 16:1669-1672.
41. Krasovskiy A., Knochel P. Convenient titration method for organometallic zinc, magnesium, and lanthanide reagents. Synthesis 2006, 5:890-891.
42. Wakami H., Yoshida J. Grignard exchange reaction using a microflow system: from bench to pilot plant. Org. Process Res. Dev. 2005, 9:787-791.
43. Petersen T.P., Becker M.R., Knochel P. Continuous flow magnesiation of functionalized heterocycles and acrylates with TMPMgCl·LiCl. Angew. Chem., Int. Ed. 2014, 53:7933-7937.
44. Brodmann T., Koos P., Metzger A., Knochel P., Ley S.V. Continuous preparation of arylmagnesium reagents in flow with inline IR monitoring. Org. Process Res. Dev. 2012, 16:1102-1113.
45. Nagaki A., Uesugi Y., Kim H., Yoshida J. Synthesis of functionalized aryl fluorides using organolithium reagents in flow microreactors. Chem. Asian J. 2013, 8:705-708.
46. Nagaki A., Ichinari D., Yoshida J. Reactions of organolithiums with dialkyl oxalates. A flow microreactor approach to synthesis of functionalized α-keto esters. Chem. Commun. 2013, 49:3242-3244.
47. Nagaki A., Yamada D., Yamada S., Doi M., Ichinari D., Tomida Y., Takabayashi N., Yoshida J. Generation and reactions of pyridyllithiums via Br/Li exchange reactions using continuous flow microreactor systems. Aust. J. Chem. 2013, 66:199-207.
48. Nagaki A., Takahashi Y., Yoshida J. Extremely fast gas/liquid reactions in flow microreactors: carboxylation of short-lived organolithiums. Chem. Eur. J. 2014, 20:7931-7934.
49. Wu J., Yang X., He Z., Mao X., Alan Hatton T., Jamison T.F. Continuous flow synthesis of ketones from carbon dioxide and organolithium or Grignard reagents. Angew. Chem., Int. Ed. 2014, 53:8416-8420.
50. Pieber B., Glasnov T., Kappe C.O. Flash carboxylation: fast lithiation-carboxylation sequence at room temperature in continuous flow. RSC Adv. 2014, 4:13430-13433.
51. Bridges A.J., Patt W.C., Stickney T.M. A dramatic solvent effect during aromatic halogen-metal exchanges. Different products from lithiation of polyfluorobromobenzenes in ether and THF. J. Org. Chem. 1990, 55:773-775.
52. Armarego W.L.F., Chai C. Purification of Laboratory Chemicals 2012, Butterworth-Heinemann.