HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → 1,3-bis(4-bromophenyl)-2-(4-tert-butylphenyl)-1H-pyrrole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | Trans-4-bromocinnamaldehyde | HCID 6285035 | — |
| Reactant | 2-(4-Bromophenylamino)-2-(4-tert-butylphenyl)acetonitrile | HCID 58226806 | — |
| Product | 1,3-bis(4-bromophenyl)-2-(4-tert-butylphenyl)-1H-pyrrole | HCID 58226609 | 10% |
Reaction Steps
To the product of Example 7.1C (0.676 g, 3.2 mmol) and the product from Example 7.1A (1.0 g, 2.91 mmol) was added ethanol (30 mL) followed by potassium hydroxide (0.163 g, 2.91 mmol), and the mixture was stirred at room temperature for 16 hours. Afterwards the mixture was concentrated. The residue was partitioned between water and ethyl acetate. The organic layers were combined, dried and then concentrated. The residue was purified by chromatography (silica gel, hexanes in ethyl acetate) which afforded 150 mg, (10%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.37 (m, 3H), 7.32 (d, J=8.5, 2H), 7.21 (d, J=8.4 Hz, 2H), 7.06 (d, J=8.3 Hz, 2H), 6.93 (m, 4H), 6.51 (dd, J=2.9 Hz, 1H), 1.29 (s, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08921514B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-981882c5583c4f1abee54b6d6969fa56 |
| Source note | uspto-grants-2014_12 |