Hexachloroethane → 5-chloro-1-(2,4-difluoro-phenyl)-1H-[1,2,4]triazole

HRID 1629143ノート

反応式

HRID 1629143 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH:13]=[N:12][CH:11]=[N:10]1.C([Li])CCC.[Cl:19]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[Cl:19][C:13]1[N:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[N:10]=[CH:11][N:12]=1

参加物

5

反応物 3

HCID 6214HexachloroethaneHCID 232945821-(2,4-difluoro-phenyl)-1H-[1,2,4]triazoleHCID 178418339Butyllithium

生成物 1

HCID 582049865-chloro-1-(2,4-difluoro-phenyl)-1H-[1,2,4]triazole収率 66.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under an atmosphere of nitrogen a solution of 1-(2,4-difluoro-phenyl)-1H-[1,2,4]triazole (15.7 g, 86.7 mmol) in THF (300 mL) at −78° C. was treated with n-butyllithium (38 mL, 2.5 M, 95.3 mmol) dropwise. After stirring for 1.5 h a solution of hexachloroethane (22.6 g, 95.3 mmol) in THF (30 mL) was added dropwise. The resultant reaction mixture was stirred for 1.5 h before allowing to warm to RT and quenching with water. The resultant mixture was diluted with water and extracted with ethyl acetate, the combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to give an oil which crystallised on standing. The solid was recrystallised from cyclohexane to give 5-Chloro-1-(2,4-difluoro-phenyl)-1H-[1,2,4]triazole (12.4 g, 66%). 1H NMR δ (ppm)(CDCl3): 8.04 (1 H, s), 7.51-7.43 (1 H, m), 7.10-7.04 (2 H, m).

後処理

  1. additionwas added dropwise
  2. customThe resultant reaction mixture
  3. customquenching with water
  4. additionThe resultant mixture was diluted with water
  5. extractionextracted with ethyl acetate
  6. dry with materialthe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give an oil which
  10. customcrystallised
  11. customThe solid was recrystallised from cyclohexane

出典と根拠

ORDレコード
ord-356f6ba49946493187c2a7cc1a3c62aa
出典データセット
uspto-grants-2014_07
特許番号
US08785626B2

反応ノート

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