Benzeneacetic acid, 4-bromo- → 1-(4-Bromophenyl)cyclohexane-1-carboxylic acid

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Reaction Steps

The title compound was obtained in a manner analogous to that for 1-Phenylcyclohexanecarboxylic acid (1/3) starting with (4-bromophenyl)acetic acid (4d), via tetrahydro-2H-pyran-2-yl 2-(4-bromophenyl)acetate (5d). The crude product 1/9 was chromatographed on silica gel with petroleum ether-dioxane-acetic acid (85:15:2) and petroleum ether-tert-butylmethyl ether-acetic acid (8:2:0.1) as eluents to give 1-(4-bromophenyl)cyclohexanecarboxylic acid (1/9) in 25% yield. 1H NMR (CDCl3, HMDSO) δ: 1.17-1.92 (8H, m); 2.28-2.59 (2H, m); 7.33 (2H, d, J=8.8 Hz); 7.47 (2H, d, J=8.8 Hz); 10.34 (1H, br s).

Provenance & Evidence