HuagongsheHuagongshe Chemistry Print Report · For research reference only
N,N'-Dimethylethylenediamine → n-(2,4-Difluorophenyl)-n,n'-dimethylethylene-1,2-diamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N,N'-Dimethylethylenediamine | HCID 8070 | — |
| Reactant | 1-Bromo-2,4-difluorobenzene | HCID 67674 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | sodium 2-methylpropan-2-olate | HCID 178418730 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | n-(2,4-Difluorophenyl)-n,n'-dimethylethylene-1,2-diamine | HCID 22052023 | — |
Reaction Steps
Combine 1-bromo-2,4-difluorobenzene (1.00 g, 5.18 mmol), N,N′-dimethylethylenediamine (2.74 g, 31.1 mmol), NaO-t-Bu (0.70 g, 7.2 mmol), Pd(dba)2 (0.060 g, 0.10 mmol) and (+)-BINAP (0.19 g, 0.31 mmol) in toluene (10 ml). Heat at 110° for 18 h, allow to cool, and extract with 1N HCl. Basify the aqueous solution with NaOH and extract with CH2Cl2. Dry, concentrate, and purify by PLC to give N-(2,4-difluorophenyl)-N,N′-dimethylethylenediamine.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06897216B2 |
| Source dataset | uspto-grants-2005_05 |
| ORD ID | ord-842e21b030ca4906ada738bdc3649c2f |
| Source note | uspto-grants-2005_05 |