HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 99113-85-6
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | 4-Bromo-2-furaldehyde | HCID 2757010 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene ethanol | HCID 21863594 | — |
| Product | 99113-85-6 | HCID 13541689 | 97% |
Reaction Steps
In a screw cap pressure tube, 4-bromofuran-2-carbaldehyde (504 mg, 2.88 mmol) and phenyl boronic acid (491.7, 4.03 mmol) were suspended in a mixture of toluene:EtOH (4:1). Na2CO3 (sat) (6.0 ml) was added. N2 was bubbled through the mixture for 5 minutes. Pd(PPh3)4 (166.4 mg, 0.05 mmol) was added. The tube was sealed and the mixture heated to reflux for 4.0 h. The mixture was allowed to cool. H2O was added and the product extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography (Pet. Ether/EtOAc 90/10→85/15) to afford the title substance in 97% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08415333B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-015c1fd2210c46c291e2f2215ee2b5a5 |
| Source note | uspto-grants-2013_04 |