Conversion of alcohols to alkyl halides
15 real reactions from the literature, on primary alcohols, benzylic alcohols and tertiary alcohols. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.
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Alcohol to alkyl halide: tetrahydrofurfuryl alcohol (a primary alcohol) with PBr3, pyridine; benzene, −5 °C gives 2-(bromomethyl)oxolane (the primary alkyl bromide).
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Alcohol to alkyl halide: 1,6-hexanediol (a primary alcohol) with HCl, H2O; toluene, Δ gives 6-chloro-1-hexanol (the primary alkyl chloride).
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Alcohol to alkyl halide: tert-butanol (a tertiary alcohol) with conc. HCl gives 2-chloro-2-methylpropane (the tertiary alkyl chloride).
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Alcohol to alkyl halide: isobutanol (a primary alcohol) with PBr3 gives 1-bromo-2-methylpropane (the primary alkyl bromide).
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Alcohol to alkyl halide: 1,10-decanediol (a primary alcohol) with HBr; 135 °C gives 1,10-dibromodecane (the primary alkyl bromide).
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Alcohol to alkyl halide: tetrahydrofurfuryl alcohol (a primary alcohol) with SOCl2; pyridine gives 2-chloromethyl tetrahydrofuran (the primary alkyl chloride).
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Alcohol to alkyl halide: 1-dodecanol (a primary alcohol) with HBr; 100 - 120 °C gives 1-bromododecane (the primary alkyl bromide).
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Alcohol to alkyl halide: 1-butanol (a primary alcohol) with ZnCl2, HCl; Δ gives butyl chloride (the primary alkyl chloride).
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Alcohol to alkyl halide: glycol monoethyl ether (a primary alcohol) with PBr3 gives 2-bromoethyl ethyl ether (the primary alkyl bromide).
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Alcohol to alkyl halide: pentaerythritol (a primary alcohol) with 48% HBr; AcOH, Δ gives 2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol (the primary alkyl bromide).
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Alcohol to alkyl halide: phenyl(2-thienyl)methanol (a benzylic alcohol) with HCl gives phenyl-2-thienylmethyl chloride (the benzylic alkyl chloride).
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Alcohol to alkyl halide: 1,6-hexanediol (a primary alcohol) with KI, ortho-phosphoric acid; phosphoric anhydride, Δ gives 1,6-diiodohexane (the primary alkyl iodide).
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Alcohol to alkyl halide: a benzylic alcohol with HBr, H2SO4 gives (Z)-2-(bromomethyl)-3-(4-formylphenyl)prop-2-enoic acid (the allylic alkyl bromide).
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Alcohol to alkyl halide: 4-methoxybenzyl alcohol (a benzylic alcohol) with HCl gives 4-methyloxybenzyl chloride (the benzylic alkyl chloride).
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Alcohol to alkyl halide: ethyl (R)-2-hydroxy-2-methylbutanoate (a tertiary alcohol) with 1) MsCl / pyridine; 2) CsF; triethylene glycol (solvent); net inversion gives the tertiary alkyl fluoride.