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Ethylene Glycol → N-benzyl-4-chloroaniline
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Ethylene Glycol | HCID 174 | — |
| 反応物 | Benzylamine | HCID 7504 | — |
| 反応物 | 1-Chloro-4-iodobenzene | HCID 12510 | — |
| 反応物 | Potassium Phosphate, Tribasic | HCID 62657 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 溶媒 | Isopropanol | HCID 3776 | — |
| 溶媒 | Ethyl acetate hexane | HCID 21226206 | — |
| 生成物 | N-benzyl-4-chloroaniline | HCID 76281 | 84% |
反応手順
The general procedure under argon was followed using copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (131 μL, 1.20 mmol), 4-chloroiodobenzene (239 mg, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate=10/1, Rf=0.4) afforded N-(4-chlorophenyl)benzylamine (182 mg, 84% isolated yield) as light yellow liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Burton, R. D.; Bartberger, M. D.; Zhang, Y.; Eyler, J. R.; Schanze, K. S. J. Am. Chem. Soc. 1996, 118, 5655-5664.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09067955B2 |
| 出典データセット | uspto-grants-2015_06 |
| ORD ID | ord-c09efdd143dd49399821d0e6bfe13515 |
| 出典メモ | uspto-grants-2015_06 |