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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2220206Generated: November 1, 2026

Tributylvinyltin → N-(4-chloro-2-vinyl-phenyl)-acetamide

https://huagongshe.com/reaction/2220206

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTributylvinyltinHCID 81998—
ReactantN-(2-bromo-4-chlorophenyl)acetamideHCID 282685—
CatalystHCID 178418476HCID 178418476—
SolventTolueneHCID 1140—
ProductN-(4-chloro-2-vinyl-phenyl)-acetamideHCID 5971761164%

Reaction Conditions

Temperature95 °C

Reaction Steps

To a stirred solution of N-(2-bromo-4-chloro-phenyl)-acetamide (2 g, 8 mmol) in toluene (20 mL) was added tributyl(vinyl)tin (3.05 mL, 10.5 mmol) and dichlorobis(triphenylphosphine)palladium (II) (1.41 g, 2 mmol). The reaction mixture was heated at 95° C. for 1 hour, and the solvent removed in vacuo. The residue obtained was purified by flash chromatography eluting with 20% ethyl acetate/CH2Cl2 to give N-(4-Chloro-2-vinyl-phenyl)-acetamide (1 g, 64%). HPLC: Rt=2.16 min. m/z=196 (M+H+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07417040B2
Source datasetuspto-grants-2008_08
ORD IDord-c7e0da0fa4614e29a3c285ba073b6a82
Source noteuspto-grants-2008_08