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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 62919Generated: October 30, 2026

Ethanol → 2-(2-Fluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl ester

https://huagongshe.com/reaction/62919

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
ReactantBoron tribromideHCID 25134—
Reactant2-(2-Fluoro-4-methoxy-phenyl)-cyclopropane carboxylic acid ethyl esterHCID 67289140—
SolventDichloromethaneHCID 6344—
Product2-(2-Fluoro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl esterHCID 90118187166.4%

Reaction Conditions

Temperature-78 °C

Reaction Steps

After 2-(2-fluoro-4-methoxy-phenyl)-cyclopropane carboxylic acid ethyl ester (0.16 g, 0.67 mmol) obtained in Step B was dissolved in anhydrous DCM (10 mL), 1M BBr3 solution (3.36 mL, 3.35 mmol) was added thereto at −78° C., and the mixture was stirred at room temperature for 3 hours. After the termination of the reaction, EtOH was added thereto, and the mixture was stirred at room temperature for 30 minutes. The reactant was concentrated under reduced pressure, added with saturated sodium bicarbonate aqueous solution, and extracted with DCM. The organic layer was concentrated under reduced pressure and purified by column chromatography (eluent, EtOAc/Hex=1/4) to obtain the title compound (0.25 g, 97%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09447044B2
Source datasetuspto-grants-2016_09
ORD IDord-5fdb96adcc1046fdb94d6c1efe673154
Source noteuspto-grants-2016_09