HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 4-(5-Fluoropyrimidin-2-yl)benzaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Chloro-5-fluoropyrimidine | HCID 583466 | — |
| Reactant | 4-Formylphenylboronic Acid | HCID 591073 | — |
| Catalyst | (Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1) | HCID 10974057 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-(5-Fluoropyrimidin-2-yl)benzaldehyde | HCID 22631252 | 52% |
Reaction Steps
A suspension of 2M aq. Na2CO3 (7 mL) and 4-formylphenylboronic acid (1.35 g, 9.0 mmol) in ethanol (4 mL) was added to a solution of 2-chloro-5-fluoropyrimidine (922 mg, 7.0 mmol, prepared as described in Org. Prep. Proc. Int. 1995, 27, 600), and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.209 g, 0.35 mmol) in toluene (15 mL). The reaction mixture was heated to reflux for 6 h, cooled to room temperature, diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried with Na2SO4, and concentrated in vacuo. Purification by medium pressure liquid chromatography (SiO2, 20:1 hexanes/ethyl acetate) gave 732 mg (52%) of the title compound. MS 203 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06825170B2 |
| Source dataset | uspto-grants-2004_11 |
| ORD ID | ord-657a15cbee0e40509cea9a8d74860a55 |
| Source note | uspto-grants-2004_11 |