Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 2-Chloropyridine | HCID 7977 | — |
| Reactant | HCID 178478979 | HCID 178478979 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-Phenylpyridine | HCID 13887 | 98.1% |
Reaction Steps
216.5 g (3.0 mol) of tetrahydrofuran (THF), 113.5 g (1.0 mol) of 2-chloropyridine and 0.24 g of Pd(dppf)Cl2 (0.03 mol %) are placed in a flask and heated to 50° C. while stirring. 510 g of phenylmagnesium chloride solution in THF (27% strength) are slowly metered in while cooling externally so that the temperature does not exceed 50° C. The mixture is then stirred for another 90 minutes at this temperature. It is slowly hydrolyzed with 250 g of water and allowed to cool to room temperature. After phase separation, the aqueous phase is stirred with 250 ml of tert-butyl methyl ether. After renewed phase separation, the organic phases combined and the reaction mixture is evaporated at 150 mbar. It is subsequently distilled at atmospheric pressure until a bottom temperature of 80° C. has been reached. The distillation residue is distilled at 10 mbar, giving 152.0 g of 2-phenylpyridine (98.1%), purity: 98.7% (according to GC).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06248892B1 |
|---|
| Source dataset | uspto-grants-2001_06 |
|---|
| ORD ID | ord-df83252ebc404baca49f0a8efc794bba |
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| Source note | uspto-grants-2001_06 |
|---|
