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In page Haloalkane:

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In the laboratory, more active deoxygenating and halogenating agents combine with base to effect the conversion. In the "Darzens halogenation", thionyl chloride (SOCl2) with pyridine converts less reactive alcohols to chlorides. Both phosphorus pentachloride (PCl5) and phosphorus trichloride (PCl3) function similarly, and alcohols convert to bromoalkanes under hydrobromic acid or phosphorus tribromide (PBr3). The heavier halogens do not require preformed reagents: A catalytic amount of PBr3 may be used for the transformation using phosphorus and bromine; PBr3 is formed in situ.[2] Iodoalkanes may similarly be prepared using red phosphorus and iodine (equivalent to phosphorus triiodide).[citation needed]