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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 629368Generated: October 26, 2026

Water → 3-Hydroxy-2-methylbenzonitrile

https://huagongshe.com/reaction/629368

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant3-Bromo-2-methylphenolHCID 11171430—
ReactantHCID 178418546HCID 178418546—
CatalystHCID 178418397HCID 178418397—
SolventDimethylformamideHCID 6228—
Product3-Hydroxy-2-methylbenzonitrileHCID 2261609449.2%

Reaction Conditions

Temperature120 °C

Reaction Steps

To a solution of 3-bromo-2-methylphenol (20.0 g) in DMF (250 mL) were added copper(I) cyanide (19.0 g) and tetrakis(triphenylphosphine)palladium(0) (3.70 g), and the mixture was heated with stirring at 120° C. for 16 hr under nitrogen atmosphere. The reaction mixture was poured into water, and the mixture was filtered. The filtrate was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was washed with tert-butyl methyl ether to give the title compound (7.00 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09315458B2
Source datasetuspto-grants-2016_04
ORD IDord-ad803e8f7a134729a6582064b93c2c91
Source noteuspto-grants-2016_04