HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → Methyl 2'-cyano-5-(1,2-dihydroxyethyl)-4'-methylbiphenyl-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl 3-bromo-5-(1,2-dihydroxyethyl)benzoate | HCID 58188335 | — |
| Reactant | 5-Methyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile | HCID 58407329 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Methyl 2'-cyano-5-(1,2-dihydroxyethyl)-4'-methylbiphenyl-3-carboxylate | HCID 58187958 | — |
Reaction Steps
A mixture of methyl 3-bromo-5-(1,2-dihydroxyethyl)benzoate (100 mg, 0.36 mmol), 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (130 mg, 0.54 mmol), tetrakis(triphenylphosphine)palladium(0) (40 mg, 0.035 mmol), potassium carbonate (75 mg, 0.54 mmol), N,N-dimethylformamide (0.5 mL), and toluene (1 mL) under nitrogen was subjected to microwave irradiation at 110° C. for 1 h. After cooling, the mixture was diluted with water (5 mL) and extracted with EtOAc (15 mL×3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by flash column to afford the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08946439B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-9c255834da3a4232aeb48a142ef71389 |
| Source note | uspto-grants-2015_02 |