Hell–Volhard–Zelinsky reaction
8 real reactions from the literature, on carboxylic acids and five-membered lactones. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.
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Hell–Volhard–Zelinsky: hexanoic acid (a carboxylic acid) with Br2, Δ; PCl3 (cat.) gives 2-bromohexanoic acid (the α-bromo acid).
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Hell–Volhard–Zelinsky: gamma-butyrolactone (a five-membered lactone) with P, Br2; Δ gives 3-bromooxolan-2-one (the α-bromo acid).
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Hell–Volhard–Zelinsky: lauric acid (a carboxylic acid) with Br2; PCl3 gives 2-bromododecanoic acid (the α-bromo acid).
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Hell–Volhard–Zelinsky: isovaleric acid (a carboxylic acid) with Br2; PCl3, Δ gives 2-bromoisovaleric acid (the α-bromo acid).
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Hell–Volhard–Zelinsky: hexanoic acid (a carboxylic acid) with 1) SOCl2, CCl4, 65 °C; 2) NBS, HBr, 85 °C gives 2-bromohexanoyl chloride (the α-bromo acid).
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Hell–Volhard–Zelinsky: isocaproic acid (a carboxylic acid) with Br2; PCl3, Δ gives 2-bromo-4-methylpentanoic acid (the α-bromo acid).
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Hell–Volhard–Zelinsky: 2-methyldodecanoic acid (a carboxylic acid) with Br2, PBr3; 90 °C gives 2-bromo-2-methyldodecanoyl bromide (the α-bromo acid).
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Hell–Volhard–Zelinsky: isobutyric acid (a carboxylic acid) with P, Br2; 100 °C gives 2-bromo-2-methylpropionyl bromide (the α-bromo acid).