Phosphorus oxychloride → 2-Chloro-4-(4-trifluoromethylphenyl)pyridine

HRID 730313

反応式

HRID 730313 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N+:12]([O-])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:13]1[CH:14]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=2)[CH:10]=[CH:11][N:12]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 573508294-(4-(Trifluoromethyl)phenyl)pyridine 1-oxide

生成物 1

HCID 288758632-Chloro-4-(4-trifluoromethylphenyl)pyridine

実験手順

To 4-(4-trifluoromethyl-phenyl)-pyridine 1-oxide (2.4 g, 10 mmol) was added phosphorous oxychloride (12 mL) at room temperature. The reaction mixture was heated at reflux for 5 h. POCl3 was removed under reduced pressure, and the residue was partitioned between EtOAc and aqueous ammonium hydroxide. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by chromatography on a Biotage 40 M column (8:1 hexanes:EtOAc) to give the title compound as a white solid. MS (ESI, pos. ion) m/z: 258.5 (M+1).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 h
  3. customPOCl3 was removed under reduced pressure
  4. customthe residue was partitioned between EtOAc and aqueous ammonium hydroxide
  5. extractionThe aqueous layer was extracted with EtOAc
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by chromatography on a Biotage 40 M column (8:1 hexanes:EtOAc)

出典と根拠

ORDレコード
ord-b9880877cfc945ae9dd7d354a2c150a8
出典データセット
uspto-grants-2009_09
特許番号
US07582657B2

関連ノート

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