Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl 5-bromosalicylate | HCID 77683 | — |
| Reactant | 4-(Trifluoromethoxy)phenylboronic acid | HCID 2734386 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 118162005 | HCID 118162005 | 84.7% |
Reaction Steps
Methyl 5-bromosalicylate (5 g, 21.6 mmol), 4-(trifluoromethoxy)phenylboronic acid (4.43 g, 21.6 mmol), potassium carbonate (10 g) and [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (800 mg, 1.09 mmol) were combined in 10 mL DMF. 5 mL water was added and the mixture was stirred at 50° C. for 60 minutes. The reaction mixture was diluted with 300 mL ethyl acetate, washed with water and brine and evaporated under vacuum. Flash chromatographic purification on 120 g silica gel with 0-100% ethyl acetate in hexane gave methyl 4-hydroxy-4′-(trifluoromethoxy)-[1,1′-biphenyl]-3-carboxylate (5.7 g, 18.3 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09416115B2 |
|---|
| Source dataset | uspto-grants-2016_08 |
|---|
| ORD ID | ord-8310f27afae94bbfa1c648e9e0dc85d6 |
|---|
| Source note | uspto-grants-2016_08 |
|---|
