Water → Bromo-2-iodoaniline

Temperature

0 °C

A vigorously stirred suspension of 2-iodoaniline (10.0 g, 45.7 mmol), potassium bromide (6.52 g, 54.8 mmol), and ammonium molybdate tetrahydrate (0.57 g, 0.46 mmol) in acetic acid (54 mL) was cooled to 0° C., treated with sodium perborate (7.74 g, 50.3 mmol), and stirred for two hours as the reaction warmed to room temperature. After adding water and stirring one additional hour, the reaction mixture was poured into ice-water and filtered. The filtered solid was washed with water, dissolved in ethyl acetate (250 mL), and washed with a saturated, aqueous, potassium carbonate solution (2×75 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford the intermediate, 4 bromo-2-iodoaniline, as a red solid (12.56 g, 92%).

1. temperaturewarmed to room temperature
2. stirringstirring one additional hour
3. filtrationfiltered
4. washThe filtered solid was washed with water
5. dissolutiondissolved in ethyl acetate (250 mL)
6. washwashed with a saturated, aqueous, potassium carbonate solution (2×75 mL)
7. dry with materialThe organic phase was dried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-1766e2435cb945218d495d97ea8dae04

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06894061B2