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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1108512Generated: October 31, 2026

p-Bromochlorobenzene → 4-Chlorobiphenyl

https://huagongshe.com/reaction/1108512

Reaction equation

Participants

RoleNameHCIDCharge
Reactantp-BromochlorobenzeneHCID 7806—
ReactantHCID 178420681HCID 178420681—
CatalystBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
SolventTetrahydrofuranHCID 8028—
Product4-ChlorobiphenylHCID 16323—

Reaction Steps

6 mol of a 26% strength by weight phenylmagnesium chloride/THF solution are added dropwise in the course of 4 hours to a boiling solution of 6 mol of 1,4-bromochlorobenzene and 100 mg of Pd(dppf)Cl2 *CH2Cl2 in 600 g of tetrahydrofuran (THF). After completion of the addition, the reaction mixture is refluxed for a further 5 hours. After hydrolysis with 3600 g of 8% strength by weight sulfuric acid, phase separation and subsequent removal of the solvent by distillation, crude 4-chlorobiphenyl is obtained, which is purified by fractional distillation in vacuo. Yield 1080 g (96%), purity of the product □ 99.7% (a/a GC).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06066766
Source datasetuspto-grants-2000_05
ORD IDord-dfb457085d52422b87da496963d25b5b
Source noteuspto-grants-2000_05