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

Temperature

90 °C

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)+.

1. temperaturecooled to 25° C.
2. extractionextracted with diethyl ether (2×150 mL) The combined organic layers
3. washwere washed with 1N NaOH (1×100 mL), water (3×100 mL) and brine (1×100 mL)
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. customevaporated

ORD record

ord-5e961637d0f94f79abfefc3ae15843db

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748627B2