Isoamyl Nitrite → 1,5-Dibromo-2-chloro-3-fluorobenzene
反応式
[Br:1][C:2]1[C:7]([Cl:8])=[C:6]([F:9])[CH:5]=[C:4]([Br:10])[C:3]=1N.C(ON=O)CC(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([Br:10])[CH:5]=[C:6]([F:9])[C:7]=1[Cl:8]参加物
4
反応条件
- 温度
- 70 °C
実験手順
A solution of 2,6-dibromo-3-chloro-4-fluoro-phenylamine (1a, 4.85 g, 16 mmol, 1 eq.) in DMF (20 mL) was added to a solution of isoamylnitrite (3.46 mL, 25.6 mmol, 1.6 eq.) in DMF (12 mL) at 70° C. The mixture was heated at 70° C. for 3 h before it was cooled to room temperature, quenched with 1 N NaOH aqueous solution (150 mL), and extracted with EtOAc (200 mL). The EtOAc extract was washed with brine (100 mL×2), dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (heptane) to give desired product 2a as colorless oil (3.70 g, 80%).
後処理
- temperaturewas cooled to room temperature
- customquenched with 1 N NaOH aqueous solution (150 mL)
- extractionextracted with EtOAc (200 mL)
- extractionThe EtOAc extract
- washwas washed with brine (100 mL×2)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography (heptane)
出典と根拠
- ORDレコード
- ord-1542332200754fccbfc72f4ce284cc5a
- 出典データセット
- uspto-grants-2015_12
- 特許番号
- US09221827B2
反応ノート
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