A facile one-pot synthesis of alpha-bromo-alpha,beta-unsaturated esters from alcohols.
Treatment of N-bromosuccinimide (NBS) with (carboethoxymethylene) triphenylphosphorane (1) in CH(2)Cl(2) 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 alpha-bromo-alpha,beta-unsaturated esters in good to excellent yield.
Karama
Usama
U
Chemistry Department, College of Science, King Saud University, P.O. Box 2455 Riyadh 11451, Saudi Arabia. Karama@ksu.edu.sa
Al-Othman
Zeid
Z
Al-Majid
Abdullah
A
Almansour
Abdulrahman
A
D000438:Alcohols / Q000737:chemistry*; D001974:Bromosuccinimide / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis*; D008722:Methods; D010753:Phosphoranes / Q000737:chemistry; D013237:Stereoisomerism; D014465:Ultrasonics
D000438:Alcohols; D004952:Esters; D010753:Phosphoranes; D001974:Bromosuccinimide