HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 2-(2'-Chlorobiphenyl-4-yl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-phenyl}propanenitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-(4-Bromophenyl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propanenitrile | HCID 67449101 | — |
| Catalyst | palladium acetate PPh3 | HCID 11554889 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | n-Propanol dioxane | HCID 67832237 | — |
| Product | 2-(2'-Chlorobiphenyl-4-yl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-phenyl}propanenitrile | HCID 67448242 | — |
Reaction Steps
To a solution 2-(4-bromophenyl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propanenitrile (1 eq.) from step 1,2-chlorophenylboronic acid (2 eq.) in n-propanol:dioxane (1:2; 0.17M) at room temperature was added palladium acetate/triphenyl phosphine (1:3; 0.05 eq.) and aqueous Na2CO3 (2M; 4 eq.). The mixture was stiffed 30 min at 150° C. in microwave (Smith Creator; Personal Chemistry), cooled to room temperature, poured in water and extracted with EtOAc. The organic extract was washed with water, brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel, eluting with Hex/EtOAc 5% afforded the desired compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08334308B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-42e34a5292b842d0833e41054358c434 |
| Source note | uspto-grants-2012_12 |