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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 561483Generated: October 31, 2026

Diethyl Ether → (4-Chlorophenyl)(2,2-difluorocyclopropyl)methanol

https://huagongshe.com/reaction/561483

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantAmmonium ChlorideHCID 25517—
ReactantSodium borohydrideHCID 4311764—
Reactant2,2-Difluorocyclopropyl(4-chlorophenyl) ketoneHCID 24865871—
SolventEthanolHCID 702—
SolventEthyl AcetateHCID 8857—
Product(4-Chlorophenyl)(2,2-difluorocyclopropyl)methanolHCID 58392413—

Reaction Conditions

Temperature40 °C

Reaction Steps

336 mg (8.89 mmol) of sodium borohydride were added to 1.75 g (8.08 mmol) of the compound from Example 124A in 33 ml of ethanol and 9 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 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 magnesium sulfate, filtered and concentrated. 1.44 g (82% 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-fc5f375805a94fe8af6a928964fd7edd
Source noteuspto-grants-2011_11