HCID 18629320, compound → HCID 18629345, compound

Participants

Reaction Steps

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).

Provenance & Evidence