Sulfuric Acid → 1-Iodo-4-nitro-2-(trifluoromethyl)benzene

Participants

Reaction Steps

To a mixture of 3.1 g (15.0 mmol) of 2-amino-5-nitrobenzotrifluoride in 60 mL of 40% (v/v) H2SO4 stirred in an ice-bath was added dropwise a solution of 2.1 g (30.4 mmol) of NaNO2 in 10 mL of H2O. The resulting yellow solution was stirred in an ice-bath for 1 h and it was added dropwise into a well stirred solution of 10 g of NaI in 250 mL of H2O cooled in an ice bath. Gas releasing and precipitate was observed. The mixture was stirred overnight at 25° C., filtered and washed by water, and dried to leave pale yellow solid (4.5 g, 94%), mp 81°-82° C. 1H NMR (CDCl3), 8.047 (dd, 1), 8.272 (d, 1), 8.483 (d, 1).

Provenance & Evidence