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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 561485Generated: October 31, 2026

Dichloromethane → 2-[(2-Chloro-4-fluorophenyl)(hydroxy)methyl]cyclopropanecarbonitrile

https://huagongshe.com/reaction/561485

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDichloromethaneHCID 6344—
ReactantSodium borohydrideHCID 4311764—
Reactant2-(2-Chloro-4-fluorobenzoyl)cyclopropanecarbonitrileHCID 58392501—
SolventEthanolHCID 702—
SolventEthyl AcetateHCID 8857—
Product2-[(2-Chloro-4-fluorophenyl)(hydroxy)methyl]cyclopropanecarbonitrileHCID 58392441—

Reaction Conditions

Temperature40 °C

Reaction Steps

409 mg (10.8 mmol) of sodium borohydride were added to 2.20 g (9.84 mmol) of the compound from Example 127A in 180 ml of ethanol and 60 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 2 h. The reaction mixture was added to dichloromethane, the phases were separated, and the organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) to result in 1.52 g (69% 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-3f7694c970b54369b45e3665c2a5eb88
Source noteuspto-grants-2011_11