Synthesis of alkyl chlorides

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Recent Literature

Nucleophilic fluorination using CsF or alkali metal fluorides was completed in short reaction time in the presence of [bmim][BF₄] affording the desired products without any byproducts. Facile nucleophilic substitutions such as halogenations, acetoxylation, nitrilation, and alkoxylations in the presence of ionic liquids provided the desired products in good yields.
D. W. Kim, C. E. Song, D. Y. Chi, J. Org. Chem., 2003, 68, 4281-4285.

The preparation of alkenyl halides of any length from inexpensive starting reagents is reported. Standard organic transformations were used to prepare straight-chain α-olefin halides in excellent overall yields with no detectable olefin isomerization and full recovery of any unreacted starting material.
T. W. Baughman, J. C. Sworen, K. B. Wagener, Tetrahedron, 2004, 60, 10943-10948.

The reaction of alcohols and β-amino alcohols with 2,4,6-trichloro[1,3,5]triazine and N,N-dimethylformamide in methylene chloride at room temperature gave the corresponding chlorides, and with NaBr gave the corresponding bromides in high yields.
L. de Luca, G. Giacomelli, A. Porcheddu, Org. Lett., 2002, 4, 553-555.

An efficient InCl₃-catalyzed reaction of secondary, tertiary and benzylic alcohols with chlorodimethylsilane in the presence of benzil gave the corresponding organic chlorides under mild conditions. In the absence of benzil, the reducing products through dehydroxyhydration were obtained.
M. Yasuda, S. Yamasaki, Y. Onishi, A. Baba, J. Am. Chem. Soc., 2004, 126, 7186-7187.

An indium(III) hydroxide-catalyzed reaction of carbonyls and chlorodimethylsilane afforded the corresponding deoxygenative chlorination products. Ester, nitro, cyano, or halogen groups were not affected during the reaction course. Typical Lewis acids such as TiCl₄, AlCl₃, and BF₃·OEt₂ showed no catalytic activity. The reaction mechanism is discussed.
Y. Onishi, D. Ogawa, M. Yasuda, A. Baba, J. Am. Chem. Soc., 2002, 124, 13690-13691.

Group 5 and 6 metal chlorides were found as very efficient catalysts for acylative cleavage of ethers. Compared with conventional Lewis acid catalysts, group 5 and 6 metal chlorides showed better results in the catalytic C-O bond cleavage.
Q. Guo, T. Miyaji, R. Hara, B. Shen, T. Takahashi, Tetrahedron, 2002, 58, 7327-7334.

Halofluorination of alkenes in the presence of trihaloisocyanuric acids and HF•pyridine results in the formation of vicinal halofluoroalkanes in good yields. The reaction is regioselective leading to Markovnikov-oriented products and the halofluorinated adducts follow anti-addition in the case of cyclohexene and 1-methylcyclohexene.
L. T. C. Crespo, R. da S. Ribeiro, M. S. S. de Mattos, P. M. Esteves, Synthesis, 2010, 2379-2382.