Sulfuric Acid → Methyl 4-bromo-2-iodobenzoate

Temperature

5 °C

To methyl 2-amino-4-bromobenzoate (5.75 g) was added cooled 20% sulfuric acid (75 mL), sodium nitrite (2.07 g) was added by small portions under ice-cooling, and the mixture was stirred at the same temperature for 40 min. To this reaction mixture was added dropwise a solution of potassium iodide (8.3 g) in water (25 mL) under cooling to 5° C., 20% sulfuric acid (30 mL) was added, and the mixture was stirred at 5° C. for 2 hr. This reaction mixture was neutralized with 4N aqueous sodium hydroxide solution under ice-cooling, 10% aqueous sodium sulfite solution (45 mL) and sodium chloride were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% aqueous sodium sulfite solution added saturated brine and saturated brine, dried over sodium sulfate, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (7.05 g).

1. additionwas added by small portions under ice-
2. temperaturecooling
3. stirringthe mixture was stirred at 5° C. for 2 hr
4. temperaturecooling
5. extractionthe mixture was extracted with ethyl acetate
6. washThe organic layer was washed with 10% aqueous sodium sulfite solution
7. additionadded saturated brine and saturated brine
8. dry with materialdried over sodium sulfate
9. customthe solvent was evaporated
10. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

ORD record

ord-9dbbe8fcc9d74f33aa5bc7b25b6a800a

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08816079B2