Diisobutylaluminum hydride → 3-(3,5-Difluorophenyl)propanal

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Reaction Conditions

Reaction Steps

The above 3-(3,5-difluorophenyl)propionic ethyl ester 53.0 g (247 mmol) was dissolved in toluene 500 ml and cooled to −58° C. under stirring, and a 1.01 M of toluene solution 255 ml (258 mmol) of DIBAL was added dropwise, and the mixture was stirred at −55° C. for 15 minutes. At the same temperature, a saturated ammonium chloride aqueous solution 200 ml was added dropwise to the reactant, and the mixture was heated to room temperature and stirred for 30 minutes. Diethyl ether 100 ml was added to the reactant, and the mixture was stirred at room temperature for one hour, and magnesium sulfate was added, and the suspension was filtered with cerite. The filtrate was washed with water, the organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 3(3,5-difluorophenyl)propanal 41.5 g. The yield was 98.8% from 3-(3,5-difluorophenyl)propionic acid ethyl ester.

Provenance & Evidence