Potassium Iodide → 2,4-Difluoro-3-iodo-1,5-dimethoxybenzene

Participants

Reaction Steps

To a stirred slurry of 2,6-difluoro-3,5-dimethoxyaniline (1.00 g, 5.29 mmol) in 6.0 M hydrogen chloride in water (9.00 mL, 54.0 mmol), a solution of sodium nitrite (0.383 g, 5.55 mmol) in water (2 mL) was added dropwise over 15 minutes at 0° C. After another 15 minutes, the resulting orange-red slurry was added to a solution of potassium iodide (3.50 g, 21.1 mmol) in water (5 mL) in small portions at 0° C. After addition, the reaction mixture was allowed to warm to room temperature and then it was stirred for 1 hour. Solid precipitated which was filtered out. The solid was washed with water and dried under vacuum to give the desired product (1.15 g, 70%). 1H NMR (400 MHz, CDCl3): δ 6.68 (t, J=8.0 Hz, 1H), 3.88 (s, 6H) ppm.

Provenance & Evidence