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

Temperature

60 °C

To stirred solution of 5-bromo-2-methyl-3-nitrobenzoic acid (285 g, 1104 mmol) in DMF (2.8 L) was added sodium carbonate (468 g, 4415 mmol) followed by addition of methyl iodide (626 g, 4415 mmol) at room temperature. The resulting reaction mixture was heated at 60° C. for 8 h. After completion, the reaction mixture was filtered and washed with ethyl acetate. The combined filtrates were washed with water and the aqueous phase was back extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to afford the title compound as an off-white solid (290 g, 97% yield). The isolated compound was taken directly into the next step.

1. customThe resulting reaction mixture
2. filtrationAfter completion, the reaction mixture was filtered
3. washwashed with ethyl acetate
4. washThe combined filtrates were washed with water
5. extractionthe aqueous phase was back extracted with ethyl acetate
6. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-287b336738a2457884a2f16e5492b2d5

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376422B2