1-(2-TRIFLUOROMETHYL-PHENYL)-CYCLOPROPANECARBOXYLIC ACID synthesis

Yield:886366-06-9 86%

Reaction Conditions:

Stage #1: 1-(2-(trifluoromethyl)phenyl)cyclopropanecarbonitrilewith lithium hydroxide;water for 72 h;Heating / reflux;
Stage #2: with hydrogenchloride in water at 20;

Steps:

To a 50 mL round-bottom flask equipped with a condenser was added intermediate 101 (1-(2-(trifluoromethyl)phenyl)cyclopropanecarbonitrile, 0.92 g, 4.4 mmol, 1.0 eq.) and 20 mL of 4.0 N LiOH solution. This suspension was heated at reflux temperature and allowed to stir for 3 days. The resulting mixture was cooled to room temperature and poured into 250 mL of 1.2 N HCl. This suspension was extracted with three 75 mL-portions of ethyl acetate and the combined organic layers were washed with three 200 mL-portions of water and 200 mL of saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered, and solvent was removed in vacuo. The desired product was obtained as a white solid (intermediate 102, 0.87 g, 86% yield). ¹H NMR (400 MHz, CDCl₃) δ 1.18-1.45 (m, 2H). 1.58-1.94 (m, J=81.09 Hz, 2H), 7.31-7.42 (m, 1H), 7.43-7.54 (m, 2H), 7.64 (d, J=7.83 Hz, 1H).

References:

US2008/255192,2008,A1 Location in patent:Page/Page column 27