Iodine → 4-Chloro-5-fluoro-2-iodoaniline

Participants

Reaction Conditions

Reaction Steps

To 4-chloro-3-fluoroaniline (25 g, 0.17 mmol) in 250 mL of H2O was added NaHCO3 (21.6 g, 0.25 mmol). After cooling to 0° C., iodine (43.5 g, 0.17 mmol) was added. After 18 h at rt, an additional 10.8 g of iodine was added and the reaction was stirred overnight. The reaction was extracted with DCM (4×250 mL), the combined organics were washed with sodium thiosulfate solution (2×250 mL) and brine (2×250 mL) and dried (Na2SO4). Purification by silica gel chromatography gave 47 g of Intermediate 5A.MS (ESI) m/z: 145.2 (M+H)+.

Provenance & Evidence