[F:1][C:2]1[C:12]([CH3:13])=[C:11](F)[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N-:15]=[N+:16]=[N-:17].[Na+].C1(C)C=CC=CC=1.O>CS(C)=O>[N:15]([C:11]1[CH:10]=[CH:9][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([F:1])[C:12]=1[CH3:13])=[N+:16]=[N-:17]In 47 ml of dimethyl sulfoxide was dissolved 4.65 g of ethyl 2,4-difluoro-3-methylbenzoate, followed by adding thereto 3.32 g of sodium azide, and the resulting mixture was stirred at 70° C. for 20 hours. The reaction mixture was cooled to room temperature and then added to a mixed solvent of 150 ml of toluene and 150 ml of water, and 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: toluene) to obtain 2.20 g of ethyl 4-azido-2-fluoro-3-methylbenzoate as a light-yellow oil.
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