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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 561486Generated: November 1, 2026

Ammonium Chloride → 2-[(2,4-Difluorophenyl)(hydroxy)methyl]cyclopropanecarbonitrile

https://huagongshe.com/reaction/561486

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmonium ChlorideHCID 25517—
ReactantSodium borohydrideHCID 4311764—
Reactant2-(2,4-Difluorobenzoyl)cyclopropanecarbonitrileHCID 58392551—
SolventEthanolHCID 702—
SolventEthyl AcetateHCID 8857—
Product2-[(2,4-Difluorophenyl)(hydroxy)methyl]cyclopropanecarbonitrileHCID 58392472—

Reaction Conditions

Temperature40 °C

Reaction Steps

342 mg (9.03 mmol) of sodium borohydride were added to 1.70 g (8.21 mmol) of the compound from Example 123A in 35 ml of ethanol and 15 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 1 h. The reaction mixture was added to saturated aqueous ammonium chloride solution and ethyl acetate, the phases were separated, the aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate 9/1) to result in 1.50 g (87% of theory) of a mixture of the diastereomers of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08063234B2
Source datasetuspto-grants-2011_11
ORD IDord-80b5b8dcd3ad4307a8e5f123e6e73631
Source noteuspto-grants-2011_11