Water → 2-Bromo-4-nitrobenzoic acid

Temperature

60 °C

2-Bromo-4-nitrotoluene (5.0 g, 23.14 mmol) was dissolved in pyridine (23 mL) and water (46 mL). The heterogeneous mixture was heated to 60° C. and KMnO4 (18.29 g, 115.7 mmol) was added carefully. The mixture was then heated under reflux overnight. The reaction mixture was filtered and washed with boiling water. The solution was then made acidic and extracted into ethyl acetate, dried over Na2SO4 and the solvent was removed in vacuo. The crude product was dissolved in aqueous NaOH and washed with hexanes. The aqueous phase was made acidic and the product was extracted into ethyl acetate. The ethyl acetate solutions were combined and dried over Na2SO4 and the solvent was removed in vacuo to provide the desired product (3.72 g): m.p. 158-160° C.;

1. temperatureThe mixture was then heated
2. temperatureunder reflux overnight
3. filtrationThe reaction mixture was filtered
4. washwashed with boiling water
5. extractionmade acidic and extracted into ethyl acetate
6. dry with materialdried over Na2SO4
7. customthe solvent was removed in vacuo
8. dissolutionThe crude product was dissolved in aqueous NaOH
9. washwashed with hexanes
10. extractionthe product was extracted into ethyl acetate
11. dry with materialdried over Na2SO4
12. customthe solvent was removed in vacuo

ORD record

ord-84ed58534e1e4a3991eb4c9262c95390

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06310095B1