Nucleophilic aromatic substitution
9 real reactions from the literature: SNAr on aryl fluorides, aryl chlorides and aryl bromides. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.
Printable worksheet (PDF): with or without products.
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SNAr: 4-bromo-5-nitroveratrole (an aryl bromide) with MeSH; K2CO3 gives (4,5-dimethoxy-2-nitrophenyl)(methyl)sulfane (the substituted arene). 79% yield.
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SNAr: 4-fluorobenzaldehyde (an aryl fluoride) and 4-methoxyphenol with K2CO3 gives 4-(4-methoxyphenoxy)benzaldehyde (the substituted arene). 89% yield.
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SNAr: homoveratrylamine (a primary amine) and 1-fluoro-2-nitrobenzene (an aryl fluoride) with iPr2NEt gives N-[2-(3,4-dimethoxyphenyl)ethyl]-2-nitroaniline (the substituted arene). 100% yield.
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SNAr: cyclohexylhydrazine (a primary amine) and 2',4'-difluoropropiophenone (an aryl fluoride) with NaOAc (weak base) gives 1-cyclohexyl-3-ethyl-6-fluoro-1H-indazole (the substituted arene). 98% yield.
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SNAr: 2,3,4-trifluorobenzoic acid (an aryl fluoride) and 2-chloro-4-iodoaniline (an aryl iodide) with excess; LiNH2 gives 2-(2-chloro-4-iodoanilino)-3,4-difluorobenzoic acid (the substituted arene). 50% yield.
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SNAr: 4,4'-bipyridine and 1-chloro-2,4-dinitrobenzene (an aryl chloride) with hint: product is a salt gives 1-(2,4-dinitrophenyl)-4-pyridin-4-ylpyridin-1-ium (the substituted arene).
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SNAr: 2,4-dichloronitrobenzene (an aryl chloride) with Na2S gives the substituted arene. 50% yield.
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SNAr: 2-fluoro-5-nitro-2'-(trifluoromethoxy)-1,1'-biphenyl (an aryl fluoride) with MeONa gives the substituted arene. 93% yield.
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SNAr: diethyl methylmalonate (a malonate ester) and 2,4-dichloro-5-fluoropyrimidine (a heteroaryl fluoride) with NaH gives the substituted arene. 98% yield.