A Facile One-Pot Synthesis of α-Bromo-α,β-unsaturated Esters from Alcohols

doi:10.3390/molecules15053276

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Molecules 2010, 15(5), 3276-3280; doi:10.3390/molecules15053276

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A Facile One-Pot Synthesis of α-Bromo-α,β-unsaturated Esters from Alcohols

Usama Karama* , Zeid Al-Othman, Abdullah Al-Majid and Abdulrahman Almansour

Chemistry Department, College of Science, King Saud University, P.O. Box 2455 Riyadh 11451, Saudi Arabia

* Author to whom correspondence should be addressed.

Received: 9 March 2010; in revised form: 27 April 2010 / Accepted: 29 April 2010 / Published: 4 May 2010

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Abstract: Treatment ofN-bromosuccinimide (NBS) with (carboethoxymethylene) triphenylphosphorane (1) in CH₂Cl₂ followed by the addition of an alcohol in the presence of manganese dioxide under ultrasonic irradiation constitutes a stereoselective one-pot procedure for the preparation of Z-configured α–bromo-α,β-unsaturated esters in good to excellent yield.

Keywords: one-pot synthesis; bromoylides; oxidation; α–bromo-α,β-unsaturated esters

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MDPI and ACS Style

Karama, U.; Al-Othman, Z.; Al-Majid, A.; Almansour, A. A Facile One-Pot Synthesis of α-Bromo-α,β-unsaturated Esters from Alcohols. Molecules 2010, 15, 3276-3280.

AMA Style

Karama U, Al-Othman Z, Al-Majid A, Almansour A. A Facile One-Pot Synthesis of α-Bromo-α,β-unsaturated Esters from Alcohols. Molecules. 2010; 15(5):3276-3280.

Chicago/Turabian Style

Karama, Usama; Al-Othman, Zeid; Al-Majid, Abdullah; Almansour, Abdulrahman. 2010. "A Facile One-Pot Synthesis of α-Bromo-α,β-unsaturated Esters from Alcohols." Molecules 15, no. 5: 3276-3280.

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