Iodine → HCID 66905441, compound

Participants

Reaction Conditions

Reaction Steps

3-Chloroaniline (12.4 ml, 118 mmol; [108-42-9]) and Na2SO4 (3.36 g, 24 mmol) were added to a solution of 4-fluoro-2-nitro-benzaldehyde (1 g, 6 mmol; [2923-96-8]) in THF (12 ml) under an argon atmosphere. The suspension was stirred at 50° C. for 16 h. Na2SO4 was removed, indium (2.04 g, 18 mmol) and iodine (1.2 g, 5 mmol) were added and the reaction mixture was stirred at 50° C. for 24 h. The mixture was filtered over celite and the filtrate was poured onto 1 M aqueous HCl solution/iPrOAc 1/1. The aqueous layer was extracted one more time with iPrOAc and the combined extracts were washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by crystallization (CH2Cl2) to give the title compound (672 mg, 1.8 mmol; 31%) as white powder. MS: m/e=372.0 [M+H+].

Provenance & Evidence