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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1411444Generated: October 26, 2026

Ethanol → 1,3-bis(4-bromophenyl)-2-(4-tert-butylphenyl)-1H-pyrrole

https://huagongshe.com/reaction/1411444

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
ReactantPotassium HydroxideHCID 14797—
ReactantTrans-4-bromocinnamaldehydeHCID 6285035—
Reactant2-(4-Bromophenylamino)-2-(4-tert-butylphenyl)acetonitrileHCID 58226806—
Product1,3-bis(4-bromophenyl)-2-(4-tert-butylphenyl)-1H-pyrroleHCID 5822660910%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08921514B2
Source datasetuspto-grants-2014_12
ORD IDord-981882c5583c4f1abee54b6d6969fa56
Source noteuspto-grants-2014_12