Hydrochloric Acid → 3-(4-Fluorophenyl)-6-(trifluoromethyl)indan-1-one

반응식

Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[CH2:13][C:14](O)=[O:15].C([Li])CCC.Cl>C(OCC)C>[F:23][C:20]1[CH:19]=[CH:18][C:17]([CH:12]2[C:3]3[C:4](=[CH:5][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][CH:2]=3)[C:14](=[O:15])[CH2:13]2)=[CH:22][CH:21]=1

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실험 절차

To a solution of 40 grams of 3-(2-bromo-4-trifluoromethylphenyl)-3-(4'-fluorophenyl)-propanoic acid in 750 milliliters of dry diethylether were added dropwise 90 milliliters of butyllithium (20% in hexane). The temperature was kept between -2 and -5 degrees Centigrade, and the addition time was about 10 minutes. The reaction mixture was stirred at zero degrees Centigrade for 11/2 hours; and then 400 milliliters of 2 N hydrochloric acid were added. The orgranic phase was separated and extracted twice with a 10% solution of sodium carbonate in water, then washed with water and dried over anhydrous potassium carbonate. After filtration and evaporation there was obtained 23 grams of crude 3-(4'-fluorophenyl)-6-trifluoromethyl-1-indanone. The oil was distilled in vacuo, and there was obtained 17 grams (57%) of pure 3-(4'-fluorophenyl)-6-trifluoromethyl-1-indanone boiling at 140 degrees Centigrade /0.2 mmHg.