関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Potassium Phosphate, Tribasic | HCID 62657 | — |
| 反応物 | 4-Bromo-2-hydroxybenzonitrile | HCID 12966961 | — |
| 反応物 | Potassium cyclopropyltrifluoroborate | HCID 23697338 | — |
| 触媒 | Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) | HCID 11714597 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 溶媒 | Ammonium chloride ethyl acetate | HCID 86583716 | — |
| 生成物 | 4-Cyclopropyl-2-hydroxybenzonitrile | HCID 86690250 | — |
反応手順
A solution of 4-bromo-2-hydroxybenzonitrile (1 g, 5.05 mmol), potassium cyclopropyltrifluoroborate (1.495 g, 10.10 mmol), K3PO4 (5.05 ml, 15.15 mmol) and PdCl2(Amphos)2 (0.358 g, 0.505 mmol) in toluene (25 mL) was allowed to stir at 100° C. under nitrogen overnight. The mixture was then cooled to room temperature, diluted with EtOAc/NH4Cl(aq), and filtered through a pad of Celite. The organic layer was seperated, dried over Na2SO4, filtered and concentrated. The residue was purified by FCC (0-50% EtOAc/heptane) to provide 4-cyclopropyl-2-hydroxybenzonitrile, 1H NMR (400 MHz, CH2Cl2) δ 12.17 (br. s., 1H), 7.23 (d, J=8.34 Hz, 1H), 6.51-6.58 (m, 2H), 1.82 (tt, J=5.02, 8.37 Hz, 1H), 0.94-1.00 (m, 2H), 0.68-0.73 (m, 2H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08846656B2 |
|---|
| 出典データセット | uspto-grants-2014_09 |
|---|
| ORD ID | ord-4c162c32089e4416946d0dfff84ac7b6 |
|---|
| 出典メモ | uspto-grants-2014_09 |
|---|
