HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 67111220, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Ethyl 5-bromofuran-2-carboxylate | HCID 345282 | — |
| Reactant | 4-Fluoro-3-(trifluoromethyl)benzeneboronic acid | HCID 17750051 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 67111220 | HCID 67111220 | 83.4% |
Reaction Steps
To a solution of ethyl 5-bromofuran-2-carboxylate (150 mg, 0.69 mmol) in DME (5 mL) were added 4-fluoro-3-(trifluoromethyl)phenylboronic acid (171 mg, 0.82 mmol), 2M Na2CO3 (1.03 mL, 2.06 mol), and catalytic amounts of Pd(Ph3)4 (158 mg, 0.14 mmol). The reaction mixture was refluxed for 5 h, diluted with water and extracted with EtOAc. The extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel (EtOAc/n-Hex=1:5) to give title compound (174 mg, 70%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08691855B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-46881bbc54d0484fbbbab19f5331b17d |
| Source note | uspto-grants-2014_04 |