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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2069078Generated: October 31, 2026

Dimethyl Sulfoxide → 2-(3-Bromo-5-methoxyphenyl)acetonitrile

https://huagongshe.com/reaction/2069078

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethyl SulfoxideHCID 679—
ReactantSodium CyanideHCID 8929—
ReactantSodium BicarbonateHCID 516892—
Reactant1-Bromo-3-(bromomethyl)-5-methoxybenzeneHCID 12276449—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Product2-(3-Bromo-5-methoxyphenyl)acetonitrileHCID 2124296586.4%

Reaction Conditions

Temperature40 °C

Reaction Steps

Sodium cyanide (3.4 g; WAKO) was added to a DMSO (100 mL) solution of Intermediate 2 (16.3 g) at room temperature and the resulting mixture was stirred at 40° C. for 1 hour and 40 minutes. Ethyl acetate (300 mL) and saturated aqueous sodium bicarbonate solution (150 mL), and water (150 mL) were added to extract the reaction mixture, the reaction mixture was washed with saturated brine (300 mL), the organic layer was dried, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Yamazen; n-hexane/ethyl acetate) to give the title compound (11.37 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08299055B2
Source datasetuspto-grants-2012_10
ORD IDord-403b95ede2c1470c813392e81959ab6c
Source noteuspto-grants-2012_10