Electrophilic aromatic nitration
12 real reactions from the literature, on acyl-deactivated arenes, alkylbenzenes, anilines and phenols. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.
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EAS nitration: resorcinol (a phenol) with HNO3; AcOH gives 4-nitroresorcinol (the nitroarene). 75% yield.
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EAS nitration: p-cymene (an alkylbenzene) with HNO3; H2SO4, AcOH; -10 to -15 °C gives 1-methyl-2-nitro-4-propan-2-ylbenzene (the nitroarene).
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EAS nitration: N,N-dimethylaniline with HNO3; H2SO4, 5 °C gives N,N-dimethyl-3-nitroaniline (the nitroarene).
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EAS nitration: N-(4-methoxyphenyl)acetamide (an anisole) with Ac2O gives N-(4-methoxy-2-nitrophenyl)acetamide (the nitroarene).
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EAS nitration: benzoic acid (an acyl-deactivated arene) with HNO3 (2 equiv.) (fuming), Δ; H2SO4 gives 3,5-dinitrobenzoic acid (the nitroarene).
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EAS nitration: benzaldehyde (an acyl-deactivated arene) with fuming HNO3; H2SO4 gives 3-nitrobenzaldehyde (the nitroarene).
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EAS nitration: acetophenone (an acyl-deactivated arene) with HNO3; H2SO4 gives m-nitroacetophenone (the nitroarene).
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EAS nitration: o-toluidine (an aniline) with 1) Ac2O; 2) HNO3, 10-12 °C; 3) aq. HCl gives 2-methyl-6-nitroaniline (the nitroarene).
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EAS nitration: methyl benzoate (an acyl-deactivated arene) with HNO3, H2SO4; 5 - 15 °C gives methyl 3-nitrobenzoate (the nitroarene).
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EAS nitration: mesitylene (an alkylbenzene) with HNO3; Ac2O, AcOH gives 2-nitromesitylene (the nitroarene).
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EAS nitration: benzene-d6 with HNO3; H2SO4 gives nitrobenzene-d5 (the nitroarene). 96% yield.
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EAS nitration: 2,4-dinitrotoluene (an alkylbenzene) with HNO3; H2SO4; 110 °C gives 2,4,6-trinitrotoluene (the nitroarene).