Water → 2-Bromo-5-(4-methoxyphenoxy)-1,3,4-thiadiazole

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Reaction Conditions

Reaction Steps

2,5-dibromo-1,3,4-thiadiazole (2 g, 8.16 mmol), (prepared according to Example 1 as described in U.S. Pat. No. 5,847,149) was dissolved in N,N-dimethyl formamide (65 mL) and the resulting solution was treated with K2CO3 (1.69 g, 12.24 mmol) and 4-methoxyphenol (1.01 g, 8.16 mmol). The reaction mixture was heated at 90° C. for 1.5 hours, cooled to 25° C., poured into water (150 mL) and extracted with diethyl ether (2×150 mL) The combined organic layers were washed with 1N NaOH (1×100 mL), water (3×100 mL) and brine (1×100 mL), dried (Na2SO4), filtered and evaporated to provide 2.3 g of a light yellow oil. The residue was purified by flash chromatography on silica gel eluting with a solvent gradient from 1% to 14% ethyl acetate in hexanes to provide 1.86 g (79%) of the title compound, 1H NMR (300 MHz, DMSO-d6) δ ppm 7.40 (d, J=9.19 Hz, 2H) 7.04 (d, J=9.19 Hz, 2H) 3.79 (s, 3H); MS (APCI) m/z 289 (M+H)+.

Provenance & Evidence