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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 588804Generated: October 29, 2026

Sodium Carbonate → 2',6-Dichloro-4-vinyl-[1,1'-biphenyl]-3-amine

https://huagongshe.com/reaction/588804

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant2-Chlorophenylboronic acidHCID 2734322—
Reactant5-Bromo-4-chloro-2-vinylbenzenamineHCID 117607165—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
Product2',6-Dichloro-4-vinyl-[1,1'-biphenyl]-3-amineHCID 9046038673.1%

Reaction Steps

A mixture of 5-bromo-4-chloro-2-vinylbenzenamine (600 mg, 2.6 mmol), 2-chlorophenylboronic acid (1.25 g, 12.9 mmol), Pd(PPh3)4 (300 mg, 0.2 6 mmol), Na2CO3 (1.4 g, 13.0 mmol) in 1,4-dioxane (20 mL) and water (5 mL) was stirred at reflux under argon for 16 h. The mixture was allowed to cool to room temperature and then concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=30:1) to afford the desired product (500 mg, 73.1% yield). ESI-MS m/z: 263.1[M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09227978B2
Source datasetuspto-grants-2016_01
ORD IDord-344f197f21054b179b7be94fe86e1664
Source noteuspto-grants-2016_01