Reaktion #216804

Reaktionsgleichung

sodium iodide

chloromethyl ethyl ether

potassium tert-butoxide

2,3-dibromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrrole

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title product

Ausbeute 74.2%

2,3-Dibromo-5-(p-chlorophenyl)-1-(ethoxymethyl)-4-[(trifluoromethyl)sulfonyl]pyrrole

Ausbeute 74.2%

Lösungsmittel

hexane

water

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for five minutes
2. 2
   workup.STIRRINGstirred at room temperature for several hours
3. 3
   Extraktionextracted with ether
4. 4
   WaschenThe combined organic extracts are washed with water and brine
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigeto give an orange oil
8. 8
   Filtrationfiltered

Vorschrift

A solution of potassium tert-butoxide (0.62 g, 0.0055 mol) in tetrahydrofuran is treated with 2,3-dibromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrrole (2.34 g, 0.005 mol), stirred for 15 minutes, treated with sodium iodide (0.82 g, 0.0055 mol), stirred for five minutes, treated with a solution of chloromethyl ethyl ether (0.52 g, 0.0055 mol) in tetrahydrofuran, stirred at room temperature for several hours, poured into water and extracted with ether. The combined organic extracts are washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give an orange oil. The oil is slurried in hexane and filtered to obtain the title product as a pale yellow solid (1.95 g, mp 133°-135° C.) which is identified by 1HNMR and 19FNMR spectral analyses.

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