Pyridine, hydrofluoride (1:1) → 5-broMo-1-fluoro-2,3-diMethylbenzene

4.00 g of 5-bromo-2,3-dimethylaniline (3-11) was dissolved in 50 ml of hydrogen fluoride-pyridine, to which under cooling with ice, 5.00 ml of an aqueous solution of 2.10 g of sodium nitrite was dropped. The resulting mixture was stirred at the same temperature for 30 minutes and further stirred at a room temperature for 1 hour, and thereafter, stirred at 85° C. for 1 hour. The reaction solution was poured into ice water and extracted with ethyl acetate and the resulting organic layer was washed with sodium bicarbonate solution, and thereafter, the resulting organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=10:1) to obtain 2.92 g of 5-bromo-1-fluoro-2,3-dimethylbenzene (3-12).

1. additionwas dropped
2. stirringfurther stirred at a room temperature for 1 hour
3. stirringstirred at 85° C. for 1 hour
4. extractionextracted with ethyl acetate
5. washthe resulting organic layer was washed with sodium bicarbonate solution
6. dry with materialthe resulting organic layer was dried over anhydrous magnesium sulfate
7. customThe solvent was removed under reduced pressure
8. customthe resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=10:1)

ORD record

ord-954bbb15b91745ae8fb65739df27bcbc

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06525066B2