Bromine → HCID 71185532, compound

Liquid bromine (1.8 g, 0.57 ml, 11.43 mmol) was added drop wise to a stirred solution of methyl-5-(4-methoxyphenyl)-4-methylthiophene-2-carboxylate (prepared according to the procedure reported in WO 2007/092751, 2.0 g, 7.62 mmol) in acetic acid (20 ml) at a temperature of about 25° C. The resulting mixture was stirred at the same temperature for 16 hours. The progress of reaction was monitored by TLC. The reaction mixture was poured onto ice water (100 ml). The mixture so obtained was extracted with ethyl acetate (3×100 ml). The separated combined organic layer was washed with 10% aqueous sodium bicarbonate solution (2×50 ml). The organic layer was then dried over anhydrous Na2SO4. The solvent was evaporated form the organic layer under reduced pressure to obtain a crude product. The crude product was further purified by flash chromatography using 15-25% ethyl acetate in hexanes as an eluent to obtain the title compound (2.35 g, 90%).

1. customprepared
2. customat a temperature of about 25° C
3. customThe progress of reaction
4. additionThe reaction mixture was poured onto ice water (100 ml)
5. customThe mixture so obtained
6. extractionwas extracted with ethyl acetate (3×100 ml)
7. washwas washed with 10% aqueous sodium bicarbonate solution (2×50 ml)
8. dry with materialThe organic layer was then dried over anhydrous Na2SO4
9. customThe solvent was evaporated form the organic layer under reduced pressure
10. customto obtain a crude product
11. customThe crude product was further purified by flash chromatography

ORD record

ord-e4b3332a90fa4838a15a28f8bde8180d

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946432B2