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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 561489Generated: October 31, 2026

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

https://huagongshe.com/reaction/561489

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantAmmonium ChlorideHCID 25517—
ReactantSodium borohydrideHCID 4311764—
Reactant2-(4-Chloro-2-fluorobenzoyl)cyclopropanecarbonitrileHCID 58392490—
SolventEthanolHCID 702—
SolventEthyl AcetateHCID 8857—
Product2-[(4-Chloro-2-fluorophenyl)(hydroxy)methyl]cyclopropanecarbonitrileHCID 58392222—

Reaction Conditions

Temperature40 °C

Reaction Steps

1.01 g (26.6 mmol) of sodium borohydride were added to 5.40 g (24.1 mmol) of the compound from Example 130A in 99 ml of ethanol and 25 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 45 minutes. The reaction mixture was added to saturated aqueous ammonium chloride solution and diethyl ether, the phases were separated, the aqueous phase was extracted twice with diethyl ether, and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. 5.25 g (96% of theory) of a mixture of the diastereomers of the title compound were obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08063234B2
Source datasetuspto-grants-2011_11
ORD IDord-332b290c8150456fbefdeb171e877268
Source noteuspto-grants-2011_11