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1,4-Dibromobenzene → 5-Hydroxy-2-(4-bromophenyl)-pyridine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1,4-Dibromobenzene | HCID 7804 | — |
| 反応物 | Sodium Bicarbonate | HCID 516892 | — |
| 反応物 | Magnesium | HCID 5462224 | — |
| 反応物 | 5-Trimethylsilyloxy-2-chloropyridine | HCID 19017088 | — |
| 触媒 | Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chloride | HCID 21654969 | — |
| 溶媒 | Diethyl Ether | HCID 3283 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 5-Hydroxy-2-(4-bromophenyl)-pyridine | HCID 19017168 | 67.2% |
反応手順
A Grignard reagent solution prepared from 0.8 g of magnesium, 8.0 g of 1,4-dibromobenzene and 50 ml of tetrahydrofuran was added dropwise at 0°-5° C. within 30 minutes to a mixture of 6.6 g of 5-trimethylsilyloxy-2-chloropyridine, 75 ml of tetrahydrofuran and 0.4 g of 1,3-bis(diphenylphosphino)-propanenickel(II) chloride. The reaction mixture was stirred for 3 hours, left to stand overnight, then adjusted to pH 8 with aqueous sodium hydrogen carbonate solution and diluted with diethyl ether. The organic phase was washed neutral with water, dried over sodium sulfate and concentrated. Chromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 4:1) yielded 5.5 g of 5-hydroxy-2-(4-bromophenyl)-pyridine.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05326497 |
| 出典データセット | uspto-grants-1994_07 |
| ORD ID | ord-7bf43c9387e74ea98eb45762e01f3f7d |
| 出典メモ | uspto-grants-1994_07 |