Alcohols, secondary, conversion into with bromine

Conversion of secondary and tertiary alcohols into the corresponding chlorides has been shown to proceed efficiently when the powdered solid alcohol is exposed to HCl in a desiccator [28]. Solid-state bromination of anilines and phenols with gaseous bromine and solid bromination reagents has been shown to proceed with higher yields than in solution [29]. 

The combination of triphenylphosphine with esters of trihaloacetic acids provides a reagent system for the stereo- and regio-selective conversion of alcohols into alkyl halides.The bromine-triphenylphosphine adduct has been used at low temperatures (-50 C in dichloromethane) for the removal of the tetrahydropyranyl protecting group from tetrahydropyranyl ethers derived from secondary and tertiary alcohols.The reactions of tertiary phosphines (and other trivalent phosphorus compounds) with iodine in aprotic solvents have received further study, a range of species being identified.The first reported study of the reactions of trivalent phosphorus compounds with monopositive astatine has led to the identification of stable complexes with triphenylphosphine, trioctylphosphine, and triethylphosphite. 

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