Sulfuric Acid → Methyl 4-bromo-2-iodobenzoate

To methyl 2-amino-4-bromobenzoate (5.75 g) was added ice-cooled 20% sulfuric acid (75 mL), sodium nitrite (2.07 g) was added by small portions under ice-cooling and the mixture was stirred for 40 min. To this reaction mixture was added dropwise a solution obtained by dissolving potassium iodide (8.3 g) in water (25 mL) under ice-cooling, 20% sulfuric acid (30 mL) was added and the mixture was stirred for 2 hr. This reaction mixture was neutralized with 4N aqueous sodium hydroxide solution under ice-cooling, and the mixture was extracted with ethyl acetate, 10% aqueous sodium sulfite solution (45 mL) and sodium chloride. The organic layer was washed once with saturated brine and 10% aqueous sodium sulfite solution, with saturated brine, and dried over sodium sulfate. The solvent was evaporated and the 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. additionTo this reaction mixture was added dropwise a solution
4. customobtained
5. temperaturecooling
6. stirringthe mixture was stirred for 2 hr
7. temperaturecooling
8. extractionthe mixture was extracted with ethyl acetate, 10% aqueous sodium sulfite solution (45 mL) and sodium chloride
9. washThe organic layer was washed once with saturated brine and 10% aqueous sodium sulfite solution, with saturated brine
10. dry with materialdried over sodium sulfate
11. customThe solvent was evaporated
12. customthe residue was purified by column chromatography (hexane:ethyl acetate)

ORD record

ord-a84009cd5ec54da8a7e3a87178f2d30e

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354401B2