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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1845310Generated: October 29, 2026

Dimethylformamide → Methyl 2'-cyano-5-(1,2-dihydroxyethyl)-4'-methylbiphenyl-3-carboxylate

https://huagongshe.com/reaction/1845310

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPotassium CarbonateHCID 11430—
ReactantMethyl 3-bromo-5-(1,2-dihydroxyethyl)benzoateHCID 58188335—
Reactant5-Methyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileHCID 58407329—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
ProductMethyl 2'-cyano-5-(1,2-dihydroxyethyl)-4'-methylbiphenyl-3-carboxylateHCID 58187958—

Reaction Steps

A mixture of methyl 3-bromo-5-(1,2-dihydroxyethyl)benzoate (100 mg, 0.36 mmol), 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (130 mg, 0.54 mmol), tetrakis(triphenylphosphine)palladium(0) (40 mg, 0.035 mmol), potassium carbonate (75 mg, 0.54 mmol), N,N-dimethylformamide (0.5 mL), and toluene (1 mL) under nitrogen was subjected to microwave irradiation at 110° C. for 1 h. After cooling, the mixture was diluted with water (5 mL) and extracted with EtOAc (15 mL×3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by flash column to afford the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08946439B2
Source datasetuspto-grants-2015_02
ORD IDord-9c255834da3a4232aeb48a142ef71389
Source noteuspto-grants-2015_02