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Methane → 2-(2,4-Difluoro-phenyl)-6-methoxy-naphthalene-1-carbaldehyde
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Methane | HCID 297 | — |
| 反応物 | Cesium fluoride | HCID 25953 | — |
| 反応物 | 2,4-Difluorophenylboronic acid | HCID 2734334 | — |
| 反応物 | Trifluoromethanesulfonic acid 1-formyl-6-methoxy-naphthalen-2-yl ester | HCID 86626531 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 溶媒 | Acetonitrile | HCID 6342 | — |
| 生成物 | 2-(2,4-Difluoro-phenyl)-6-methoxy-naphthalene-1-carbaldehyde | HCID 57552553 | 62% |
反応手順
Combine trifluoromethanesulfonic acid 1-formyl-6-methoxy-naphthalen-2-yl ester (2.53 g, 7.6 mmol) with dichlorobis(triphenylphosphine)palladium (II) (0.53 g, 0.8 mmol), cesium fluoride (5.75 g, 37.8 mmol), and 2,4-difluorophenylboronic acid (2.39 g, 15.1 mmol) in acetonitrile (25 mL). Heat to reflux for 1 hour. Cool to room temperature, add DARCO, and filter. Concentrate in vacuo, dilute with dichloromethane and wash with saturated aqueous sodium carbonate. Dry the organic layer over magnesium sulfate, filter, add silica gel, and concentrate in vacuo. Purify the residue by column chromatography using an eluent of 1.5:1 hexanes:dichloromethane to give 1.4 g of the title compound (62%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08217032B2 |
| 出典データセット | uspto-grants-2012_07 |
| ORD ID | ord-082f5f66022d4158b9848a6aeb68f97b |
| 出典メモ | uspto-grants-2012_07 |