HuagongsheHuagongshe Chemistry Print Report · For research reference only
Aniline → (4-tert-Butyl-phenyl)-phenyl-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Aniline | HCID 6115 | — |
| Reactant | 1-Bromo-4-tert-butylbenzene | HCID 77595 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Solvent | Nitrogen | HCID 947 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | (4-tert-Butyl-phenyl)-phenyl-amine | HCID 11447459 | 99.2% |
Reaction Steps
96.4 g (452 mmol) of 1-bromo-4-tert-butylbenzene and 42.1 g (452 mmol) of aniline are dissolved in toluene and saturated with N2 for 15 min. 2.85 g (5 mmol) of DPPF, followed by 1.13 g (5 mmol) of Pd(OAc)2 and 56.8 g (588 mmol) of NaOtBu are subsequently added successively, and the mixture is refluxed for 6 h. The organic phase is separated off, washed twice with water and filtered through Celite, rinsed with toluene and evaporated in a rotary evaporator, leaving 101 g of ochre-coloured solid (99% of theory), which is employed without further purification in the subsequent reaction.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07799875B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-63384d02642f4c8a864c899477d2ccbb |
| Source note | uspto-grants-2010_09 |