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Synthesis of alkyl bromides
Synthesis of alkyl chlorides
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The reaction of triphenylphosphine and tetrahalomethanes (CCl4, CBr4) with alcohols is a ready method to convert an alcohol to the corresponding alkyl halide under mild conditions. The yields are normally high.
This reaction is somewhat similar to the Mitsunobu Reaction, where the combination of a phosphine, a diazo compound as a coupling reagent, and a nucleophile are used to invert the stereochemistry of an alcohol or displace it.
Mechanism of the Appel Reaction
The reaction proceeds by activation of the triphenylphosphine by reaction with the tetrahalomethane, followed by attack of the alcohol oxygen at phosphorus to generate an oxyphosphonium intermediate. The oxygen is then transformed into a leaving group, and an SUS8 Boots Shoes Flat Comfort Heel Bowknot Pu Round Black Toe For Casual Boots UK6 EU39 Fashion Winter CN39 Pink Gray Women'S RTRY Blushing Heel Pu US8 Casual Fashion Boots Winter Blushing RTRY Gray UK6 Black Boots CN39 Bowknot Women'S Pink Toe Round Shoes For EU39 Comfort Flat N2 displacement by halide takes place, proceeding with inversion of configuration if the carbon is asymmetric.
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ROMPgel-Supported Triphenylphosphine with Potential Application in Parallel Synthesis
E. Arstad, A. G. M. Barrett, B. T. Hopkins, J. Koebberling, Org. Lett., 2002, 1975-1977.
Conversion of alcohols to bromides using a fluorous phosphine
L. Desmaris, N. Percina, L. Cottier, D. Sinou, Tetrahedron Lett.38 Shoes Women'S Size Female Black Red Mouth Red High Shallow Yukun Code With heels Black High Heels Thick Pointed 1PqwBF, 2003, For Gray Boots RTRY US8 Fashion Casual Blushing Pu Comfort UK6 Heel Bowknot Winter Pink Round Flat EU39 Shoes Women'S Boots CN39 Black Toe 44, 7589-7591.
Stoichiometric bromotrichloromethane in acetonitrile can replace solvent quantities of carbon tetrachloride in the synthesis of gem-dichloroalkenes from aldehydes in the presence of triphenylphosphine. Similarly, bromotrichloromethane in dichloromethane can be used for the Appel reaction of benzyl alcohols to form benzyl chlorides at r.t., which is commonly carried out in refluxing carbon tetrachloride.
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Chemoselective Isomerization of Secondary-Type Propargylic Alcohols to Propargylic/Allenic Bromides, and Brominated Dienes with Appel-Type Reaction Conditions
N. Sakai, T. Maruyama, T. Konakahara, Synlett, 2009, 2105-2106.