Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | N,N'-Dimethylethylenediamine | HCID 8070 | — |
| Reactant | Dodecane | HCID 8182 | — |
| Reactant | Potassium Cyanide | HCID 9032 | — |
| Reactant | Benzene, 1-bromo-3,5-dimethyl- | HCID 136357 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3,5-Dimethylbenzonitrile | HCID 89718 | 15% |
Reaction Steps
A Schlenk tube was charged with CuI (19.5 mg, 0.102 mmol, 20 mol %), KCN (78 mg, 1.20 mmol), evacuated, backfilled with Ar. N,N′-Dimethylethylenediamine (21.5 μL, 0.202 mmol, 20 mol %), 5-bromo-m-xylene (136 μL, 1.00 mmol), and toluene (1.0 mL) were added under Ar. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 110° C. for 24 h. Dodecane (internal GC standard, 230 μL), ethyl acetate (2 mL), and 30% aq ammonia (1 mL) were added. A 0.1 mL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC to provide a 15% yield of 3,5-dimethylbenzonitrile.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06867298B2 |
|---|
| Source dataset | uspto-grants-2005_03 |
|---|
| ORD ID | ord-a04f30ff7576452387f28e1e0f9d1c5b |
|---|
| Source note | uspto-grants-2005_03 |
|---|
