Water → HCID 18629320, compound

In 45.3 g of 2,3-dimethylnitrobenzene was uspended 0.6 g of iron powder, followed by adding dropwise thereto 57.5 g of bromine on an oil bath at 75° C., and the resulting mixture was stirred at the same temperature for 3.5 hours. The reaction mixture was cooled to room temperature and then added to a mixed solvent of 200 ml of ethyl acetate and 200 ml of water, and the organic layer was separated. The organic layer obtained was washed with an aqueous sodium thiosulfate solution and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The resulting residue was dissolved in 200 ml of methanol and 200 ml of concentrated hydrochloric acid, followed by adding thereto 50.0 g of iron powder by portions, and the resulting mixture was stirred at 70° C. for 30 minutes. The reaction mixture was cooled to room temperature and then added to a mixed solvent of 300 ml of ethyl acetate and 300 ml of water, and the pH was adjusted to 10 with potassium carbonate, after which the organic layer was separated. The organic layer obtained was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The resulting residue was purified by a column chromatography (eluent; n-hexane:ethyl acetate=10:1) to obtain 22.6 g of 5-bromo-2,3-dimethylaniline as a colorless oil.

1. additionby adding dropwise
2. customthe organic layer was separated
3. customThe organic layer obtained
4. washwas washed with an aqueous sodium thiosulfate solution
5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
6. distillationdistilled under reduced pressure
7. customto remove the solvent
8. dissolutionThe resulting residue was dissolved in 200 ml of methanol
9. additionby adding
10. temperatureThe reaction mixture was cooled to room temperature
11. additionadded to a mixed solvent of 300 ml of ethyl acetate and 300 ml of water
12. customafter which the organic layer was separated
13. customThe organic layer obtained
14. washwas washed with water
15. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
16. distillationdistilled under reduced pressure
17. customto remove the solvent
18. customThe resulting residue was purified by a column chromatography (eluent; n-hexane:ethyl acetate=10:1)

ORD record

ord-696ccd4f4a3c439dae9025eaefa43e2c

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06025370