HCID 18629320, compound → HCID 18629345, compound

10.00 g of 5-bromo-2,3-dimethylaniline (3-11) was dissolved in a mixed solution of 50 ml of 25% sulfuric acid and 50 ml of toluene, and under cooling with ice, 20 ml of aqueous solution of 3.80 g of sodium nitrite was dropped thereto. The resulting mixture was stirred at the same temperature for 1 hour, and then stirred at 100° C. for 1 hour, and thereafter, the reaction solution was poured into ice water and extracted with ethyl acetate and the resulting organic layer was washed with saturated salt water, and thereafter, the resulting organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=9:1) to obtain 5.49 g of 5-bromo-2,3-dimethylphenol (3-17).

1. additionwas dropped
2. stirringstirred at 100° C. for 1 hour
3. extractionextracted with ethyl acetate
4. washthe resulting organic layer was washed with saturated salt water
5. dry with materialthe resulting organic layer was dried over anhydrous magnesium sulfate
6. distillationThe solvent was distilled off under reduced pressure
7. customthe resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=9:1)

ORD record

ord-64f0ce475118482e8a3c362408d77c69

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06525066B2