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Friedel–Crafts acylation

10 real reactions from the literature, on alkylbenzenes, halobenzenes, anthracenes and cyclic anhydrides. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Friedel–Crafts acylation: 1,3-difluorobenzene (a halobenzene) with AlCl3 gives 2-chloro-1-(2,4-difluorophenyl)ethanone (the aryl ketone). 91% yield.
    Friedel–Crafts acylationBioorg. Med. Chem. Lett. 2012, 22, 4887

  2. Friedel–Crafts acylation: phenylacetyl chloride (an alkylbenzene) with AlCl3 gives 2-phenylacetophenone (the aryl ketone).
    Friedel–Crafts acylationOrg. Synth. Coll. Vol. 2, p. 156

  3. Friedel–Crafts acylation: anthracene with CH3COCl; AlCl3, 0 °C, benzene gives 9-acetylanthracene (the aryl ketone).
    Friedel–Crafts acylationOrg. Synth. Coll. Vol. 4, p. 8

  4. Friedel–Crafts acylation: succinic anhydride (a cyclic anhydride) with AlCl3, Δ gives 3-benzoylpropionic acid (the aryl ketone).
    Friedel–Crafts acylationOrg. Synth. Coll. Vol. 2, p. 81

  5. Friedel–Crafts acylation: acenaphthene (a naphthalene) and succinic anhydride (a cyclic anhydride) with AlCl3; nitrobenzene; 0 °C gives 4-(1,2-dihydroacenaphthylen-5-yl)-4-oxobutanoic acid (the aryl ketone).
    Friedel–Crafts acylationOrg. Synth. Coll. Vol. 3, p. 6

  6. Friedel–Crafts acylation: pyrogallol (a phenol) with (CH3CO)2O; ZnCl2, AcOH; 140 - 145 °C gives gallacetophenone (the aryl ketone).
    Friedel–Crafts acylationOrg. Synth. Coll. Vol. 2, p. 304

  7. Friedel–Crafts acylation: thioanisole with AlCl3 gives 1-(4-(methylthio)phenyl)ethan-1-one (the aryl ketone). 79% yield.
    Friedel–Crafts acylationSulfur Lett. 1991, 12, 123

  8. Friedel–Crafts acylation: chroman (an anisole) with AlCl3 gives 1-(3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-one (the aryl ketone). 85% yield.
    Friedel–Crafts acylationAngew. Chem. Int. Ed. 2019, 58, 15386

  9. Friedel–Crafts acylation: p-anisoyl chloride (an acid chloride) and benzofuran with AlCl3 gives 3-(4'-methoxybenzoyl)benzofuran (the aryl ketone). 85% yield.
    Friedel–Crafts acylationBioorg. Med. Chem. 2018, 26, 2984

  10. Friedel–Crafts acylation: 2-[4-(2-methylpropyl)phenyl]propanoic acid (an alkylbenzene) and isobutylbenzene (an alkylbenzene) with AlCl3 gives 4'-isobutylacetophenone (the aryl ketone).
    Friedel–Crafts acylationRealOChem worksheet