Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1022834Generated: November 2, 2026

Sodium Carbonate → 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde

https://huagongshe.com/reaction/1022834

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantTriethylsilaneHCID 12052—
Reactant3-(4-Bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazoleHCID 23159812—
SolventDimethylformamideHCID 6228—
Product4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehydeHCID 8665852076.2%

Reaction Conditions

Temperature65 °C

Reaction Steps

A mixture of 3-(4-bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (14.20 g, 31.34 mmol), triethyl silane (10.3 mL, 7.53 g, 62.8 mmol), sodium carbonate (5.43 g, 39.3 mmol), palladium bis(diphenylphosphine)-ferrocene dichloride CH2Cl2-complex (1.28 g, 1.57 mmol) and DMF (250 mL) were stirred under an atmosphere of carbon monoxide at 65° C. over night. After cooling to room temperature, the solvent was evaporated and the residue taken up in MTBE (methyl-tert-butyl ether), filtered and the filtrate was concentrated in vacuum. Purification of the residue on silica gel afforded the title compound (9.60 g, 76%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08722673B2
Source datasetuspto-grants-2014_05
ORD IDord-61ddfaa702614e328bd7f3aec0405dc9
Source noteuspto-grants-2014_05