Dimethylformamide → 5-Bromo-2-chloro-3-nitropyridine

HRID 1485517

反応式

HRID 1485517 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](=O)[NH:6][CH:7]=1.CN(C=O)C.O=P(Cl)(Cl)[Cl:19]>>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([Cl:19])=[N:6][CH:7]=1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 851475-Bromo-3-nitro-2-pyridone

生成物 1

HCID 70194125-Bromo-2-chloro-3-nitropyridine収率 85%

実験手順

To a solution of 5-bromo-3-nitropyridin-2(1H)-one (4.62 g, 21.10 mmol) in POCl3 (46.2 ml) was added DMF (4.62 ml, 59.7 mmol) at room temperature. The mixture was refluxed for 2 hours, and then cooled to room temperature and concentrated in vacuo. The residue was treated with saturated aq. NaHCO3 and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=3:1) to give 5-bromo-2-chloro-3-nitropyridine (4.24 g, 85%) as a yellow solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 8.37 (1H, d, J=2.4 Hz), 8.70 (1H, d, J=2.0 Hz).

後処理

  1. temperatureThe mixture was refluxed for 2 hours
  2. concentrationconcentrated in vacuo
  3. additionThe residue was treated with saturated aq. NaHCO3
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on SiO2 (Hex:EtOAc=3:1)

出典と根拠

ORDレコード
ord-ac60d0e5e6884b69b696ccae93017adc
出典データセット
uspto-grants-2016_08
特許番号
US09422298B2

関連ノート

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