HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid → 1-(4-Bromophenyl)-2,3-dimethyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | 4-Bromoaniline | HCID 7807 | — |
| Reactant | 1-[4-(Methylsulfonyl)phenyl]-3-methylpentane-1,4-dione | HCID 21862839 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 1-(4-Bromophenyl)-2,3-dimethyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole | HCID 22316768 | 67% |
Reaction Steps
A mixture of 1-[4-(methylsulfonyl)phenyl]-3-methylpentane-1,4-dione (110 mg, 0.41 mmol), 4-bromoaniline (71 mg, 0.41 mmol), and p-toluenesulfonic acid (10 mg) in toluene (3 mL) was heated at reflux temperature using Dean-Stark apparatus. After cooling down, volatiles were removed by evaporation. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/3) to give the subtitle compound (110 mg, 67% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06294558B1 |
| Source dataset | uspto-grants-2001_09 |
| ORD ID | ord-6456bcd6cb804adcb71930b934ad5c3e |
| Source note | uspto-grants-2001_09 |