HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Methoxyaniline → 2-methoxyphenylaniline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Methoxyaniline | HCID 7000 | — |
| Reactant | Bromobenzene | HCID 7961 | — |
| Reactant | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 2-methoxyphenylaniline | HCID 10910514 | — |
Reaction Steps
A 1 L three neck flask was charged with 2-methoxyaniline (17.65 g, 143 mmol) , bromobenzene (15 g, 96 mmol), Pd2(dba)3 (1.75 g, 1.91 mmole), S-Phos (1.56 g, 3.82 mmol), sodium tert-butoxide (18.36 g, 101 mmol) and 400 mL of xylene. The reaction mixture was refluxed for 4 hours. The product was isolated by column chromatography (5% EtOAc in hexanes) to yield the desired product. (18 g, 94%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08748011B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-935d78f8a3594b03a6db292ffe1e8519 |
| Source note | uspto-grants-2014_06 |