HuagongsheHuagongshe Chemistry Print Report · For research reference only
Aniline → Diphenylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Aniline | HCID 6115 | — |
| Reactant | Bromobenzene | HCID 7961 | — |
| Reactant | Tris(1,1-dimethylethyl)phosphine | HCID 83681 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Diphenylamine | HCID 11487 | 86% |
Reaction Steps
The above general procedure was followed using bromobenzene (157 mg, 1.00 mmol) and aniline (93 mg, 1.00 mmol) with 1 mol % Pd(dba)2 and 0.8 mol % tri-t-butylphosphine in 1.5 mL of toluene. After one hour, the reaction mixture was adsorbed onto silica gel and chromatographed with 5% ethyl acetate/hexanes to give 145 mg (86%) of diphenylamine as a grey solid. 1H NMR (500 MHz, C6D6) δ 7.11-7.08 (m, 4H), 6.85-6.80 (m, 6H), 4.97 (br s, 1H). 13C NMR (125 MHz, C6D6) δ 143.6, 129.5, 121.1, 118.2. In addition, 21 mg (8%) of triphenylamine was isolated.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06100398 |
| Source dataset | uspto-grants-2000_08 |
| ORD ID | ord-3115883701cc443999b8aa5a59b08207 |
| Source note | uspto-grants-2000_08 |