HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Bromochlorobenzene → 4-Chlorobiphenyl
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Bromochlorobenzene | HCID 7806 | — |
| Reactant | HCID 178420681 | HCID 178420681 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-Chlorobiphenyl | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06066766 |
| Source dataset | uspto-grants-2000_05 |
| ORD ID | ord-dfb457085d52422b87da496963d25b5b |
| Source note | uspto-grants-2000_05 |