Hydrochloric Acid → 5-Bromo-3-fluoro-2-iodobenzoic acid

Temperature

0 °C

Sulfuric acid (47.0 mL, 882 mmol) was added to a mixture of 2-amino-5-bromo-3-fluorobenzoic acid hydrobromide (16.34 g, 51.9 mmol) and HCl (12.45 mL, 156 mmol) at 0° C. The resulting slurry was stirred at 0° C. and sodium nitrite (3.58 g, 51.9 mmol) in water (20 mL) was added dropwise over 10 minutes. The reaction was stirred 40 minutes at 0° C. before a solution of potassium iodide (17.23 g, 104 mmol) in water (20.00 mL) was added dropwise. The solution was stirred allowed to warm to RT, leading to the formation of a viscous mixture. After 1 hour at ambient temperature, the reaction was poured into ice water (500 mL) and the resulting precipitate was filtered. The black solid was washed with well water to give a dark brown solid which was dried in a vacuum oven at 50° C. for 12 hours to afford 5-bromo-3-fluoro-2-iodobenzoic acid as an orange/tan solid. MS m/z=344.8 [M+H].

1. additionwas added dropwise
2. stirringThe solution was stirred
3. temperatureto warm to RT
4. filtrationthe resulting precipitate was filtered
5. washThe black solid was washed with well water
6. customto give a dark brown solid which
7. customwas dried in a vacuum oven at 50° C. for 12 hours

ORD record

ord-34f0ca7233b942c4aa01f13b51117f87

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08883782B2