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8431155 
Journal Article 
The use of bromotrichloromethane in chlorination reactions 
Newman, SG; Bryan, CS; Perez, D; Lautens, M 
2011 
1 
Synthesis
ISSN: 0039-7881
EISSN: 1437-210X 
2 
342-346 
English 
Carbon tetrachloride is no longer used as a common solvent due to its toxicity and harmful environmental impact. The synthesis of gem-dichloroalkenes from aldehydes by using triphenylphosphine typically requires carbon tetrachloride as a solvent. We report that stoichiometric bromotrichloromethane in acetonitrile can be used in place of solvent quantities of carbon tetrachloride in this transformation. Similarly, bromotrichloromethane in dichloromethane can be used for the room-temperature Appel reaction of benzyl alcohols to form benzyl chlorides, which is commonly carried out in refluxing carbon tetrachloride. © Georg Thieme Verlag Stuttgart New York. 
aldehydes; Appel reaction; benzyl halides; halogenation; olefination