HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Benzyloxy-2-bromo-5-methoxy-benzaldehyde → HCID 86590422, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Benzyloxy-2-bromo-5-methoxy-benzaldehyde | HCID 968840 | — |
| Reactant | HCID 69817207 | HCID 69817207 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 86590422 | HCID 86590422 | 54.3% |
Reaction Steps
To a stirred solution of 3-methoxy-4-tributylstannanyl-benzoic acid methyl ester (16g, 35 mmol) and 4-benzyloxy-2-bromo-5-methoxy-benzaldehyde (9.4 g, 29 mmol) in acetonitrile (150 mL) were added CuI (5.5 g, 29 mmol) and Pd(dppf)Cl2 (4.2 g, 6 mmol). The resulting mixture was refluxed for 14 h under argon and concentrated. The residue was purified by column chromatography (4:1 hexane/EtOAc) to provide 5′-benzyloxy-2′-formyl-2,4′-dimethoxy-biphenyl-4-carboxylic acid methyl ester (6.4 g, 54%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06825208B2 |
| Source dataset | uspto-grants-2004_11 |
| ORD ID | ord-48d1f605f6e34e0cb4568bbcbb89db12 |
| Source note | uspto-grants-2004_11 |