Ethyl 2-bromo-2-phenylpropanoate → 2-Phenyl-2-[4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)-phenoxy]-propionic acid

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Reaction Steps

A solution of 4.6 g. of sodium in 140 ml. of methanol is combined with 27.55 g. of 1-methyl-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydroquinoline hydrochloride. The mixture is agitated for 30 minutes at 20°, and then 25.7 g. of 2-bromo-2-phenylpropionic acid ethyl ester is added dropwise thereto and the mixture is refluxed thereafter for 4 hours. After concentrating the mixture by evaporation, the residue is combined with water and extracted with chloroform. From the organic phase, the ethyl ester of 2-phenyl-2-[4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)-phenoxy]-propionic acid is obtained as a yellow oil; nD20 = 1.5738.

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