Methyl iodide → Methyl 5-bromo-2-methyl-3-nitrobenzoate

Temperature

60 °C

To a stirred solution of 5-bromo-2-methyl-3-nitrobenzoic acid (16 g, 61.5 mmol) in DMF (160 mL), was added iodomethane (35.7 g, 248 mmol) and sodium carbonate (26.3 g, 248 mmol). The resulting reaction mixture was stirred at 60° C. for 8 h. On completion, the reaction mixture was filtered and the inorganic solid residue washed with ethyl acetate. The combined filtrates were concentrated under vacuum till dry and re-dissolved in ethyl acetate before washing with 5% sodium bicarbonate solution (700 mL) followed by 5M HCl solution (300 mL). The organic layer was finally washed with brine, dried over sodium sulfate and concentrated to afford pure methyl 5-bromo-2-methyl-3-nitrobenzoate (16 g, 94.5%).

1. customThe resulting reaction mixture
2. filtrationOn completion, the reaction mixture was filtered
3. washthe inorganic solid residue washed with ethyl acetate
4. concentrationThe combined filtrates were concentrated under vacuum
5. customtill dry
6. dissolutionre-dissolved in ethyl acetate
7. washbefore washing with 5% sodium bicarbonate solution (700 mL)
8. washThe organic layer was finally washed with brine
9. dry with materialdried over sodium sulfate
10. concentrationconcentrated

ORD record

ord-46eed31b06cb4a90ad939c0e227d63a4

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598167B1