Potassium Iodide → 1-Fluoro-4-iodo-2-methoxybenzene

Participants

Reaction Steps

Dissolve 4-fluoro-3-methoxyphenylamine (5.0 g, 35 mmol) in water (25 mL) and concentrated sulfuric acid (8 mL). Cool to less than 0° C. in an ice/methanol bath and add sodium nitrite (2.7 g, 39 mmol) dropwise in a solution in water (20 mL) and stir one h. Dissolve potassium iodide (9.9 g, 60 mmol) in water (35 mL) and add dropwise. Warm to room temperature and stir 18 h. Extract with ethyl acetate (300 mL), wash with water (200 mL), saturated aqueous sodium thiosulfate (300 mL), and saturated aqueous sodium chloride (300 mL). Dry (sodium sulfate), filter, and concentrate to give the title compound as an orange oil (8.8 g, 99%).

Provenance & Evidence