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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 514505Generated: October 31, 2026

Dimethylformamide → Methyl 4-cyano-2-ethylbenzoate

https://huagongshe.com/reaction/514505

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantMethyl 4-bromo-2-ethylbenzoateHCID 53797189—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
CatalystHCID 178418397HCID 178418397—
ProductMethyl 4-cyano-2-ethylbenzoateHCID 6664377840%

Reaction Conditions

Temperature100 °C

Reaction Steps

Charged methyl 4-bromo-2-ethylbenzoate (1.9 g, 7.85 mmol), Zn(CN)2 (1.48 g, 12.56 mmol), Pd(PPh3)4 (1.0 g, 0.94 mmol) and DMF (30 mL) to a flask, the system was then purged with nitrogen and heated at 100° C. for 6 h. The reaction mixture was then filtered. The filtrate was extracted with ethyl acetate and concentrated the organic phase for flash column chromatograph to give 0.6 g of the title compound (40%). 1H NMR (400 MHz, CDCl3): δ 1.24 (3H, t, J=7.6 Hz), 2.99 (2H, q, J=7.6 Hz), 3.92 (3H, s), 7.52-7.54 (1H, m), 7.57 (1H, s), 7.90 (1H, d, J=8.0 Hz).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09107916B2
Source datasetuspto-grants-2015_08
ORD IDord-630f8402e7564715886823994e9f6342
Source noteuspto-grants-2015_08