HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → 5-Methoxy-[1,1'-biphenyl]-3-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | 3-Bromo-5-methoxybenzonitrile | HCID 25067362 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 5-Methoxy-[1,1'-biphenyl]-3-carbonitrile | HCID 70654473 | 91.7% |
Reaction Steps
3-bromo-5-methoxybenzonitrile (8.3 g, 39.1 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (S-Phos) (1.286 g, 3.13 mmol), phenylboronic acid (5.84 g, 47.0 mmol), Pd2(dba)3 and 200 mL toluene were charged in a flask and refluxed overnight. The reaction was cooled down and 200 mL of ethyl acetate was added. The crude mixture was run though a silica gel plug, and the product was confirmed by GC. After distillation under vacuum, 7.5 g of a white product was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08871361B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-d498e7d55f294cc1931146d566d34271 |
| Source note | uspto-grants-2014_10 |