HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → 4-Methyl-N-(4-methylphenyl)-N-{4-[2-(4-methylphenyl)ethenyl]phenyl}aniline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | 4-Bromotoluene | HCID 7805 | — |
| Reactant | 4-Aminostyrene | HCID 73700 | — |
| Reactant | Ethyl acetate hexane | HCID 21226206 | — |
| Reactant | sodium 2-methylpropan-2-olate | HCID 178418730 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | HCID 10870287 | HCID 10870287 | 11% |
| Product | 4-Methyl-N-(4-methylphenyl)-N-{4-[2-(4-methylphenyl)ethenyl]phenyl}aniline | HCID 54229592 | 84% |
Reaction Steps
Following the general procedure shown above, Pd2dba3 (18.3 mg, 2 mol %), NaO-t-Bu (336 mg, 3.5 mmol), P(isoBuNCH2CH2)3N (13.6 mg, 4 mol %), 4-aminostyrene (119 mg, 1 mmol), 4-bromotoluene (547 mg, 3.2 mmol), and 10 mL of dry toluene at 110° C. for 16 h produced (4) 4-ethenyl-N,N-bis(4-methylphenyl)benzenamine (32 mg, 11%) as a viscous liquid and (5) N,N-bis(4-methylphenyl)-4-[2-(4-methylphenyl)ethenyl]benzenamine (325 mg, 84%) as a yellow solid after chromatography with 1% EtOAc/hexane mixture. Total yield=95%. (See Entry 1 of Table 2).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07276627B2 |
| Source dataset | uspto-grants-2007_10 |
| ORD ID | ord-6a47b82b54b746fd9bd69d93b59116d2 |
| Source note | uspto-grants-2007_10 |