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Electrophilic aromatic halogenation

16 real reactions from the literature, on alkylbenzenes, biphenyls, phenols and naphthalenes. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. EAS halogenation: 4-nitrotoluene (an alkylbenzene) with Br2; Fe gives 2-bromo-4-nitrotoluene (the aryl bromide). 66% yield.
    EAS halogenationJ. Phys. Chem. A 2017, 121, 5110

  2. EAS halogenation: 4-nitrotoluene (an alkylbenzene) with Fe, Br2; 80 °C gives 2-bromo-4-nitrotoluene (the aryl bromide).
    EAS halogenationOrg. Synth. Coll. Vol. 4, p. 114

  3. EAS halogenation: acetophenone (an acyl-deactivated arene) with 1) AlCl3; 2) Br2, AlCl3; 3) H+, H2O gives 3'-bromoacetophenone (the aryl bromide).
    EAS halogenationOrg. Synth. Coll. Vol. 5, p. 117

  4. EAS halogenation: biphenyl with Br2 gives 4,4'-dibromobiphenyl (the aryl bromide).
    EAS halogenationOrg. Synth. Coll. Vol. 4, p. 256

  5. EAS halogenation: nitrobenzene (a nitroarene) with Br2, Fe; 140 °C gives 1-bromo-3-nitrobenzene (the aryl bromide).
    EAS halogenationOrg. Synth. Coll. Vol. 1, p. 123

  6. EAS halogenation: 2,4-dihydroxybenzoic acid (a phenol) with Br2; AcOH gives 5-bromo-2,4-dihydroxybenzoic acid (the aryl bromide).
    EAS halogenationOrg. Synth. Coll. Vol. 2, p. 100

  7. EAS halogenation: 4-methylacetanilide with Br2 gives N-(2-bromo-4-methylphenyl)acetamide (the aryl bromide).
    EAS halogenationOrg. Synth. Coll. Vol. 1, p. 111

  8. EAS halogenation: benzene with I2, HNO3 gives iodobenzene (the aryl iodide).
    EAS halogenationOrg. Synth. Coll. Vol. 1, p. 323

  9. EAS halogenation: 2-(N-isopropylamino)-3''-chloropropiophenone (a halobenzene) and 1-phenyl-1-propanone (an aryl ketone) with Early step in synthesis; Cl2 / AlCl3 gives 3'-chloropropiophenone (the aryl chloride).
    EAS halogenationRealOChem worksheet

  10. EAS halogenation: phenol with Br2; CS2, 5 °C gives 4-bromophenol (the aryl bromide).
    EAS halogenationOrg. Synth. Coll. Vol. 1, p. 128

  11. EAS halogenation: 2-chloro-6-fluorotoluene (an alkylbenzene) with Br2; Fe gives 1-bromo-2-chloro-4-fluoro-3-methylbenzene (the aryl fluoride). 98% yield.
    EAS halogenationJ. Med. Chem. 2009, 52, 7186

  12. EAS halogenation: veratrole (an anisole) with I2, CF3CO2Ag; CHCl3 gives 4-iodo-1,2-dimethoxybenzene (the aryl iodide).
    EAS halogenationOrg. Synth. Coll. Vol. 4, p. 547

  13. EAS halogenation: 3-fluorobiphenyl with Br2; FeCl3 gives 4-bromo-3'-fluorobiphenyl (the aryl fluoride). >80% yield.
    EAS halogenationNature 2019, 567, 223

  14. EAS halogenation: tert-butylbenzene (an alkylbenzene) with Br2; Fe gives 1-bromo-4-tert-butylbenzene (the aryl bromide). 75% yield.
    EAS halogenationJ. Am. Chem. Soc. 1944, 66, 914

  15. EAS halogenation: 1-methylnaphthalene with Br2 / Fe, cat. I2 gives 1-bromo-4-methylnaphthalene (the naphthyl bromide). 94% yield.
    EAS halogenationJ. Org. Chem. 2016, 81, 8544

  16. EAS halogenation: 2-methylnaphthalene with Br2 / Fe, cat. I2 gives 1-bromo-2-methylnaphthalene (the naphthyl bromide). 83% yield.
    EAS halogenationJ. Org. Chem. 2016, 81, 8544