Issue 0, 1987

Thallium(III) nitrate-mediated efficient synthesis of 2-arylpropionic acids from 1-halogenoethyl aryl ketones

Abstract

Treatment of 1-halogenoethyl aryl ketones [4′-RC6H4COCH(X)Me](1; R = H, Bui, OMe, Me, Ph, or Br; X = Br or Cl) with Tl(NO3)3·3H2O and perchloric acid in a trialkyl orthoformate at 25–50 °C affords alkyl esters (3) of 2-arylpropionic acid in good-to-excellent yields via 1,2-aryl migration in substrates (1). The hydrolysis of esters (3) leads to the corresponding acids, some of which are pharmaceutically important compounds. The reaction hardly occurs in methanol. The key step of the reaction is the in situ acetal formation of the starting ketone. The thallium(III) salt acts as an effective Lewis acid catalyst for both acetal formation and halide abstraction.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1987, 1255-1257

Thallium(III) nitrate-mediated efficient synthesis of 2-arylpropionic acids from 1-halogenoethyl aryl ketones

T. Yamauchi, K. Nakao and K. Fujii, J. Chem. Soc., Perkin Trans. 1, 1987, 1255 DOI: 10.1039/P19870001255

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