Identification | More | [Name]
3'-TRIFLUOROMETHYLBIPHENYL-4-CARBOXYLIC ACID | [CAS]
195457-70-6 | [Synonyms]
AKOS BAR-0024 RARECHEM AL BE 1367 4-[3-(trifluoromethyl)phenyl]benzoate 4-(3-(Trifluoromethyl)phenyl)benzoic acid 3'-TRIFLUOROMETHYLBIPHENYL-4-CARBOXYLIC ACID 3'-(TRIFLUOROMETHYL)-1,1'-BIPHENYL-4-CARBOXYLIC ACID [1,1'-BIPHENYL]-4-CARBOXYLIC ACID, 3'-(TRIFLUOROMETHYL)- | [Molecular Formula]
C14H9F3O2 | [MDL Number]
MFCD03424607 | [Molecular Weight]
266.22 | [MOL File]
195457-70-6.mol |
Hazard Information | Back Directory | [Uses]
4-(3-Trifluoromethylphenyl)benzoic Acid is a reagent used in the synthesis of aryl-substituted aspartic acid and diaminopropionic acid derivatives as inhibitors of glutamate transporter EAAT-2 (Excitatory amino acid transporters 2). | [Synthesis]
The general procedure for the synthesis of 4-(3-trifluoromethylphenyl)benzoic acid from 4-bromobenzoic acid and 3-(trifluoromethyl)phenylboronic acid was as follows: Pd(dppf)Cl2 (1.49 mmol, 1.09 g) was added to a mixture containing 4-bromobenzoic acid (14.9 mmol, 3.0 g), 3-(trifluoromethyl)phenylboronic acid (17.9 mmol, 3.4 g), and Cs2CO3 (37.3 mmol, 12.2 g) in a suspension with the solvent being a mixture of 30 mL dioxane and 7.5 mL ethanol. The reaction mixture was stirred at 80 °C for 2 hours. After completion of the reaction, it was cooled to room temperature, the solid product was collected by filtration and washed with methanol. The filtrate was concentrated and the residue was partitioned between ethyl acetate and 1N aqueous hydrochloric acid. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. To the concentrated residue was added dichloromethane, the resulting solid was collected by filtration, washed with dichloromethane and dried to give 4-(3-trifluoromethylphenyl)benzoic acid (3.58 g, 86% yield), which could be used in the next reaction without further purification. | [References]
[1] Patent: US2013/102584, 2013, A1. Location in patent: Paragraph 0307; 0308 [2] Journal of Medicinal Chemistry, 1997, vol. 40, # 20, p. 3144 - 3150 |
|
|