Sandmeyer reaction
9 real reactions from the literature, on anilines. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.
Loading examples…
-
Sandmeyer: 2,4,5-trichloroaniline with 1) HCl / NaNO2; 2) KI, heat (diazotization/Sandmeyer-type) gives 1,2,4-trichloro-5-iodobenzene (the aryl chloride). 75% yield.
-
Sandmeyer: 3-nitroaniline with 1) HCl, NaNO2; 2) CuCl gives 1-chloro-3-nitrobenzene (the aryl chloride).
-
Sandmeyer: 2,6-dinitroaniline with 1) NaNO2, N2SO4, AcOH; 2) HCl, Cu2Cl2 gives 1-chloro-2,6-dinitrobenzene (the aryl chloride).
-
Sandmeyer: p-toluidine (an aniline) with 1) H2SO4, NaNO2; H2O; 2) HBr, CuBr gives 4-bromotoluene (the aryl bromide).
-
Sandmeyer: o-toluidine (an aniline) with 1) HCl (2 equiv.), NaNO2; 2) CuCN gives 2-methylbenzonitrile.
-
Sandmeyer: 3-nitroaniline with 1) NaNO2, aq. H2SO4; 2) H2SO4, H2O, 160 °C gives 3-nitrophenol.
-
Sandmeyer: 5-methyl-2,4-dinitroaniline with tBuONO; CuCl2 gives 5-chloro-2,4-dinitrotoluene (the aryl chloride). 92% yield.
-
Sandmeyer: an aniline with NaNO2; H2SO4 / H2O gives the aryl bromide. 91% yield.
-
Sandmeyer: 8-amino-1-tetralone (an aniline) with 1) HBr / NaNO2; 2) CuBr gives 8-bromo-3,4-dihydro-2H-naphthalen-1-one (the aryl bromide). 95% yield.