Chemistry:3-Chloropyridine
3-Chloropyridine is an aryl chloride and isomer of chloropyridine with the formula C5H4ClN. It is a colorless liquid that is mainly used as a building block in organic synthesis.[1]
The compound is a substrate for many coupling processes including the Heck reaction,[2] Suzuki reaction,[3] and Ullmann reaction.[4]
Preparation
3-Chloropyridine may be prepared by the direct chlorination of pyridine with aluminium chloride used as the catalyst. The yield is 33%.[5]
A less expensive way of preparing 3-chloropyridine consists of the gas phase pyrolysis of a mixture of pyrrole and chloroform in an empty glass tube. The molar ratio of the reagents is one to five. The yields range from 25 to 33%. A little 2-chloropyridine is formed as a side product.[6] The process is thought to be an example of the Ciamician–Dennstedt rearrangement.
Pyrolytic Ciamician-Dennstedt rearrangement leading to 3-chloropyridine
References
- ↑ Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399.
- ↑ Littke, Adam F.; Fu, Gregory C. (2001). "A Versatile Catalyst for Heck Reactions of Aryl Chlorides and Aryl Bromides under Mild Conditions". Journal of the American Chemical Society 123 (29): 6989–7000. doi:10.1021/ja010988c. PMID 11459477.
- ↑ Littke, Adam F.; Dai, Chaoyang; Fu, Gregory C. (2000). "Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions". Journal of the American Chemical Society 122 (17): 4020–4028. doi:10.1021/ja0002058.
- ↑ Alonso, Diego A.; Nájera, Carmen; Pacheco, M Carmen (2002). "Highly Active Oxime-Derived Palladacycle Complexes for Suzuki−Miyaura and Ullmann-Type Coupling Reactions". The Journal of Organic Chemistry 67 (16): 5588–5594. doi:10.1021/jo025619t. PMID 12153256.
- ↑ Pearson, D. E.; Hargrove, W. W.; Chow, Judith K. T.; Suthers, B. R. (1961). "The Swamping Catalyst Effect. III. The Halogenation of Pyridine and Picolines". Journal of the American Chemical Society 26 (3): 790–791. doi:10.1021/jo01062a036.
- ↑ Rice, H. L.; Londergan, T. E. (1955). "An Improved Synthesis for 3-Chloropyridine". Journal of the American Chemical Society 77 (17): 4678. doi:10.1021/ja01622a077.
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