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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1260890Generated: November 1, 2026

Ethanol → 3-Fluoro-5-(hydroxymethyl)benzonitrile

https://huagongshe.com/reaction/1260890

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
ReactantLithium borohydrideHCID 4148881—
ReactantMethyl 3-cyano-5-fluorobenzoateHCID 26597287—
SolventTetrahydrofuranHCID 8028—
Product3-Fluoro-5-(hydroxymethyl)benzonitrileHCID 6866225262.5%

Reaction Conditions

Temperature55 °C

Reaction Steps

(Step 2) To a mixed solution of methyl 3-cyano-5-fluorobenzoate (0.55 g) obtained in Step 1 in tetrahydrofuran:ethanol=10:1 (22 ml) was added lithium tetrahydroborate (0.10 g) at 0° C. After stirring at 55° C. for 1 hr, the reaction solution was quenched with ice and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 3-fluoro-5-(hydroxymethyl)benzonitrile (0.29 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08470859B2
Source datasetuspto-grants-2013_06
ORD IDord-8bfef8f7a0554b469c0a79b4e87b200c
Source noteuspto-grants-2013_06