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, 61.54 mmol) in DMF (160 mL), iodomethane (35.72 g, 248 mmol) and sodium carbonate (26.28 g, 248 mmol) were added. Resulting reaction mass was stirred at 60° C. for 8 h. On completion, reaction mass was filtered and inorganic solid residue washed with ethyl acetate. Combined filtrate was concentrated under vacuum till dryness. The residue was re-dissolved in ethyl acetate and washed with 5% sodium bicarbonate solution (700 mL) followed by 5M HCl solution (300 mL). Organic layer was finally washed with brine, dried over sodium sulfate, filtered and concentrated to afford the desired compound (16 g. 94.50%).

1. customResulting
2. customreaction mass
3. customOn completion, reaction mass
4. filtrationwas filtered
5. washinorganic solid residue washed with ethyl acetate
6. concentrationCombined filtrate was concentrated under vacuum till dryness
7. dissolutionThe residue was re-dissolved in ethyl acetate
8. washwashed with 5% sodium bicarbonate solution (700 mL)
9. washOrganic layer was finally washed with brine
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-6cb273f47f744aa6b0c9ac071d544440

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376422B2