1-chloro-4-nitrosobenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Chloro-4-nitroso-benzene (9.1 g, 64 mmol; [932-98-9]) was added to a solution of 4,5-difluoro-2-iodo-phenylamine (10.9 g, 43 mmol; [847685-01-2]) in acetic acid (430 ml). The reaction mixture was heated under reflux conditions for 14 h. Ice water (1 l) and EtOAc (1 l) was added, the layers were separated and the aqueous layer was extracted two times with EtOAc. The combined extracts were washed with water and brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, CH2Cl2/heptane) to give the title compound (4.34 g, 11 mmol; 27%) as orange solid. MS: m/e=377.9 [M+]. The reaction mixture was heated under reflux conditions for 14 h the layers were separated the aqueous layer was extracted two times with EtOAc The combined extracts were washed with water and brine dried over Na2SO4 The solvent was removed under reduced pressure the residue was purified by column chromatography (silica gel, CH2Cl2/heptane)