| Identification | Back Directory | [Name]
4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoic acid | [CAS]
864725-62-2 | [Synonyms]
Fluralaner Impurity 2
Fluralaner Impurity 3
4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid
4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoic acid | [Molecular Formula]
C18H12Cl2F3NO3 | [MOL File]
864725-62-2.mol | [Molecular Weight]
418.19 |
| Chemical Properties | Back Directory | [Boiling point ]
511.3±60.0 °C(Predicted) | [density ]
1.49±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C Refrigerator | [pka]
3.61±0.25(Predicted) | [InChI]
InChI=1S/C18H12Cl2F3NO3/c1-9-4-10(2-3-14(9)16(25)26)15-8-17(27-24-15,18(21,22)23)11-5-12(19)7-13(20)6-11/h2-7H,8H2,1H3,(H,25,26) | [InChIKey]
KBWVSPGZOPXKRR-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=CC=C(C2CC(C3=CC(Cl)=CC(Cl)=C3)(C(F)(F)F)ON=2)C=C1C |
| Hazard Information | Back Directory | [Uses]
4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoic acid is an organic intermediate compound used in the synthesis of Fluralaner. | [Synthesis]
4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoic acid is prepared by the reaction of 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid and 3-bromo-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole. The steps are as follows:
In a 100 mL three-necked flask, under nitrogen protection, add 3-bromo-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (700 mg, 1.93 mmoL), 2-methyl-4-(4,4,5,5-tetramethyl-1,3-dioxaborolan-2-yl)benzoic acid (560 mg, 2.14 mmoL), potassium acetate (379 mg, 3.86mmol), 1,4-dioxane (15mL), water (1.5mL) and Pd(dppf)Cl2 (141mg, 0.19mmol), incubate the reaction at 85±5 for 8h, stop heating to room temperature, then Water (50 mL) was added to quench and then extracted with dichloromethane (45 mL×2), the organic phases were combined, the organic phase was washed once with saturated brine (50 mL), and then the organic phase was washed with anhydrous sodium sulfate (10.0 g). ) was dried for 2 h, the organic phase was concentrated to dryness under reduced pressure, and the concentrated residue was purified by silica gel column chromatography (developing solvent: n-heptane/ethyl acetate=10:1-3:1) to obtain 4-(5-(3 ,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid (694 mg, 86%) as a pale yellow solid.
![4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoic acid synthesis](/NewsImg/2023-12-14/6383816879086095745364124.png "4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoic acid synthesis") |
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