Bromine → methyl 3-bromo-5-(4-chlorophenyl)-1,4-dimethyl-1H-pyrrole-2-carboxylate

Bromine (1.69 g, 0.54 ml, 10.54 mmol) was added dropwise to a stirred solution of methyl-5-(4-chlorophenyl)-1,4-dimethyl-1H-pyrrole-2-carboxylate (compound 49α, 1.85 g, 7.03 mmol) in acetic acid (20 ml) at 10° C. The resulting reaction mixture was stirred at room temperature for 15 hr. The progress of the reaction was monitored by TLC. Acetic acid was removed from the reaction mixture under reduced pressure and residue obtained was dissolved in ethyl acetate (150 ml). The mixture so obtained was washed with saturated sodium bicarbonate solution (50 ml) followed by washing with brine (50 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated from the dried organic layer under reduced pressure to obtain a crude product, which was washed with a mixture of ethyl acetate in hexanes (10:90) to obtain the title compound (2.1 g, 87.5%)

1. customThe resulting reaction mixture
2. customAcetic acid was removed from the reaction mixture under reduced pressure and residue
3. customobtained
4. customThe mixture so obtained
5. washwas washed with saturated sodium bicarbonate solution (50 ml)
6. washby washing with brine (50 ml)
7. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
8. customThe solvent was evaporated from the dried organic layer under reduced pressure
9. customto obtain a crude product, which
10. washwas washed with a mixture of ethyl acetate in hexanes (10:90)

ORD record

ord-a186d4c0e80e405fb4fce91e21bb1188

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09393247B2