Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 2-Bromo-5-fluorotoluene | HCID 96743 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Product | 4-Fluoro-2-methylbenzonitrile | HCID 3826055 | — |
Reaction Steps
Into 20 ml of DMF was dissolved 10 g of 1-bromo-4-fluoro-2-methylbenzene, and then 0.2 ml of water was added. Then, 3.72 g of zinc cyanide, 484 mg of 1,1′-bis(diphenylphosphino)ferrocene, and 484 mg of tris(dibenzylideneacetone)dipalladium were added thereto under an argon stream, followed by 2 hours of stirring at 140° C. The reaction solution was ice-cooled, ammonium chloride, aqueous ammonia, and water were added thereto, and the resulting solid was collected by filtration. Then, the solid was washed with methanol and the washing liquid was concentrated to obtain 5.7 g of the title compound as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07666873B2 |
|---|
| Source dataset | uspto-grants-2010_02 |
|---|
| ORD ID | ord-d8e12994f89241c3bcd8891020d603dc |
|---|
| Source note | uspto-grants-2010_02 |
|---|
