Water → 5-broMo-1-fluoro-2,3-diMethylbenzene

Temperature

60 °C

In 50 ml of 42% borofluoric acid was suspended 5.00 g of 5-bromo-2,3-dimethylaniline, followed by adding dropwise thereto 3.9 ml of an aqueous solution of 1.80 g of sodium nitrite under ice-cooling, and the resulting mixture was stirred at the same temperature for 1 hour. The crystals precipitated were collected by filtration, dried under reduced pressure, and then heated at 60° C. on an oil bath. At the time when a theoretical amount of nitrogen was produced, the reaction mixture was cooled to room temperature and then added to a mixed solvent of 50 ml of ethyl acetate and 50 ml of water, and the organic layer was separated. The organic layer obtained was washed with 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=30:1) to obtain 2.90 g of 5-bromo-2,3-dimethylfluorobenzene as a colorless oil.

1. additionby adding dropwise
2. customThe crystals precipitated
3. filtrationwere collected by filtration
4. customdried under reduced pressure
5. customAt the time when a theoretical amount of nitrogen was produced
6. temperaturethe reaction mixture was cooled to room temperature
7. customthe organic layer was separated
8. customThe organic layer obtained
9. washwas washed with a saturated aqueous sodium chloride solution
10. dry with materialdried over anhydrous magnesium sulfate
11. distillationdistilled under reduced pressure
12. customto remove the solvent
13. customThe resulting residue was purified by a column chromatography (eluent; n-hexane:ethyl acetate=30:1)

ORD record

ord-6cf40bca48184cf78d065a89fd1b5600

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06025370