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

HRID 886118노트

반응식

HRID 886118 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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 (1H, s), 7.51-7.43 (1H, m), 7.10-7.04 (2H, m).

후처리

  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

출처 및 근거

ORD 기록
ord-3ae2ed5e0c1942e6ac6cf67a2e10614a
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242104B2

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