Bromine → HCID 71185516, compound

Temperature

25 °C

Liquid bromine (0.58 g, 0.19 ml, 3.60 mmol) was added to a solution of methyl 5-(4-methoxyphenyl)-3,4-dimethylthiophene-2-carboxylate (step-3, 0.83 g, 3.00 mmol) in acetic acid (20 ml) under stirring at 25° C. The reaction mixture was then stirred at 25° C. for 3 hrs. The progress of the reaction was monitored by TLC. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (100 ml). The resulting mixture was washed with saturated sodium bicarbonate solution (30 ml). The separated organic layer was concentrated under reduced pressure to obtain a crude product. The crude product obtained was purified by flash column chromatography using 5% ethyl acetate in hexanes as an eluent to obtain the title compound 9d (0.91 g, 83.0%).

1. stirringThe reaction mixture was then stirred at 25° C. for 3 hrs
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
4. washThe resulting mixture was washed with saturated sodium bicarbonate solution (30 ml)
5. concentrationThe separated organic layer was concentrated under reduced pressure
6. customto obtain a crude product
7. customThe crude product obtained
8. customwas purified by flash column chromatography

ORD record

ord-0a1734f12cfd4f10b472964564193c97

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946432B2