関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Methanol | HCID 887 | — |
| 反応物 | Lithium Carbonate | HCID 11125 | — |
| 反応物 | 3-Chloro-p-toluonitrile | HCID 88894 | — |
| 触媒 | Palladium Chloride | HCID 24290 | — |
| 触媒 | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| 生成物 | Methyl 5-cyano-2-methylbenzoate | HCID 9989736 | 50% |
反応手順
A solution of 3-chloro-4-methylbenzonitrile (25.0 g, 0.165 mol) in methanol (250 mL) in a steel reaction vessel was treated with lithium carbonate (13.4 g, 0.182 mol) and PdCl2.dppf (6.75 g). The vessel was purged with nitrogen, sealed, and heated to 140° C. at 400 psi for 17 hours, filtered and concentrated. The concentrate was treated with ethyl acetate, washed with saturated NaHCO3, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash chromatography on silica gel with 95:5 to 85:15 hexanes/ethyl acetate to provide 14.4 g (50%) of the desired product. MS (DCI/NH3) m/z 193.0 (M+NH4)+; 1H NMR (CDCl3) δ 8.22 (d, 1H), 7.67 (dd, 1H), 7.37 (d, 1H), 3.93 (s, 3H), 2.68 (s, 3H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US07211595B2 |
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| 出典データセット | uspto-grants-2007_05 |
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| ORD ID | ord-6cd35102c56348cbbb0f024b5472186a |
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| 出典メモ | uspto-grants-2007_05 |
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