[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[S-:9][C:10]#[N:11].[Na+].[Na+].[Br-].BrBr.C([O-])(O)=O.[Na+]>CO>[CH3:1][C:2]1[CH:7]=[C:6]([S:9][C:10]#[N:11])[CH:5]=[CH:4][C:3]=1[OH:8]
To a 250 ml flask were added 10.8 g o-methylphenol, 26.0 g sodium thiocyanate, 70 ml methanol, added dropwise 100 ml methanol solution containing 10.3 g NaBr, 5.3 ml liquid bromine at 0° C. under N2 atmosphere. The mixture was stirred at room temperature for 3 hours. The mixture was neutralized with saturated NaHCO3 solution, extracted with CH2Cl2 for four times. The extract was dried over anhydrous Na2SO4, filtrated, evaporated and purified by column chromatograph (petroleum ether:ethyl acetate=8:1) to obtain 11.1 g yellow solid, yield 67.27%. 1H-NMR (400 MHz, CDCl3, δ ppm) δ 2.2558 (3H, s), 5.0 (1H, s), 6.8 (1H, d, J=8.4 Hz), 7.3605-7.2631 (1H, m), 7.3542 (1H, s).
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