3-(4-Fluorobenzoyl)propionic acid

beige granular powder

4-(4-FIuorophenyI)-4-oxobutanoic acid 142. To a stirred mixture of succinic anhydride (1.0OgDichloromethane (50 ml) was added to a 250 ml reaction flask, 10.6 g (0.11 mol) of fluorobenzene and 14.7 g (0.11 mol) of anhydrous aluminum trichloride were added. The reaction mixture was stirred evenly in an ice-water bath, and succinic anhydride was slowly added dropwise 10.1. After 100percent of a solution of g (0.1 mol) in methylene chloride was added dropwise, the temperature was gradually raised to reflux and the reaction was carried out for 2 hours. After the reaction is completed, add 150ml of water, cool to 0°C, add 100ml of concentrated hydrochloric acid, stir at room temperature for 1 hour, stand for stratification, wash the organic layer with saturated aqueous sodium bicarbonate solution and saturated brine 150ml, and concentrate to dryness under reduced pressure. HPLC The purity was 98.0percent, and it was purified by recrystallization from toluene to obtain 16.3 g of 4-(4-fluorophenyl)-4-oxobutanoic acid in a yield of 83percent. The purity by HPLC was 99.8percent, and the content of ortho-substitution by-product was 0.03percent.In a 500 ml three-necked reaction flask equipped with a mechanical stirrer, a condenser, and a thermometer, 17.1 g (0.171 mol) of succinic anhydride and 105 g (1.09 mol) of fluorobenzene were added and dissolved with stirring. 60 g (0.306 mol) of anhydrous aluminum chloride was added in one portion, The mixture was stirred at 100 ° C for 2 hours, and decomposed by adding 165 ml of hydrochloric acid at a concentration of 10percent for 30 minutes.The other product was obtained in the same manner as in Example 1, m.p. 105-107 ° C, the yield of this step was 81.5percent, and the overall yield was 46.7percent4-(4-Fluoro-phenyl)-4-oxo-butyric acid. Succinic anhydride (1.0 g, 0.01 mmol) was dissolved in 4-fluorobenzene (3.75 mL; 0.04 mmol) and cooled to -9 General procedure: AlCl3 (1.0 g, 7.5 mmol)was added portion-wise to a solution of succinic anhydride (0.5 g, 5 mmol) and anaromatic compound (6 mmol) in CH2Cl2 (5 mL) at room temperature. The mixture wasstirred at room temperature for overnight, and the mixture was poured into 1N HClsolution (10 mL), extracted with ethyl acetate (15 mL x 3). The organic layer was driedover MgSO4. The solvent was removed under reduced pressure, and the crude productwas purified by recrystallized from ethyl acetate and hexane.Fluorobenzene (50 mL, 530 mmol) and aluminum trichloride (156 g, 1.17 mol) were added to 500 mL of methylene chloride, and the reaction mixture was stirred. Succinic anhydride (50 g, 500 mmol) was added to the stirrring reaction mixture all at once, and the reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched by cautious addition of 10percent HCl, and the reaction mixture was added to 500 mL of water. The aqueous mixture was extracted twice with 250 mL of methylene chloride, and the combined organic layers were dried (MgSOFluorobenzene (50 mL, 530 mmol) and aluminum trichloride (156 g, 1.17 mol) were added to 500 mL of methylene chloride, and the reaction mixture was stirred. Succinic anhydride (50 g, 500 mmol) was added to the stirrring reaction mixture all at once, and the reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched by cautious addition of 10percent HCl, and the reaction mixture was added to 500 mL of water. The aqueous mixture was extracted twice with 250 mL of methylene chloride, and the combined organic layers were dried (MgSOStep 1: 4-(4-Fluoro-phenyl)-4-oxo-butyric acid Fluor obenzene (50 mL, 530 mmol) and aluminum trichloride (156 g, 1.17 mol) were added to 500 mL of methylene chloride, and the reaction mixture was stirred. Succinic anhydride (50 g, 500 mmol) was added to the stirrring reaction mixture all at once, and the reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched by cautious addition of 10percent HCl, and the reaction mixture was added to 500 mL of water. The aqueous mixture was extracted twice with 250 mL of methylene chloride, and the combined organic layers were dried (MgSOStep 1: Preparation 27-Benzenesulfonγl-3, 4-dihγdro-2H-naphthalen-l-oneThe synthetic procedure described in this Preparation was carried out according to the process shown in Scheme E.

Molecular Weight:196.17
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:196.05357231
Monoisotopic Mass:196.05357231
Topological Polar Surface Area:54.4
Heavy Atom Count:14
Complexity:219
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes