Hydrochloric Acid → 5-Chloro-2-(2,2,2-trifluoroethoxy)benzonitrile

HRID 1600199

반응식

HRID 1600199 반응식
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].Cl[C:10]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:11]=1[C:12]#[N:13].Cl>CN(C)C=O>[Cl:18][C:15]1[CH:16]=[CH:17][C:10]([O:6][CH2:5][C:4]([F:8])([F:7])[F:3])=[C:11]([CH:14]=1)[C:12]#[N:13]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 890002,5-Dichlorobenzonitrile

생성물 1

HCID 190751615-Chloro-2-(2,2,2-trifluoroethoxy)benzonitrile수율 59.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Under a nitrogen atmosphere, in a round-bottom flask were placed 880 mg (22mmol) of 60% sodium hydride (NaH) and 12 ml of N,N-dimethylformamide. To the system were added 2.9 ml (4 g, 40 mmol) of 2,2,2-trifluoroethanol via syringe over a period of 15 minutes and the mixture was stirred at room temperature for 20 minutes. To the system were added 1.72 g (10 mmol) of 2,5-dichlorobenzonitrile, and the mixture was heated at 90° C. for three days. The mixture was cooled to room temperature, poured into 50 ml of 2M aqueous HCl and extracted with three portions of ether. The combinedorganic fractions were dried (Na2SO4) and concentrated to afford2.5 g of a solid. The crude material was purified by flash column chromatography using 1:49 ethyl acetate/hexanes as the eluant to obtain 1.4 g of 5-chloro-2-(2,2,2-trifluoroethoxy)benzonitrile as a white solid.

후처리

  1. customUnder a nitrogen atmosphere, in a round-bottom flask were placed
  2. temperaturethe mixture was heated at 90° C. for three days
  3. temperatureThe mixture was cooled to room temperature
  4. extractionextracted with three portions of ether
  5. dry with materialThe combinedorganic fractions were dried (Na2SO4)
  6. concentrationconcentrated to afford2
  7. customThe crude material was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-1c685416802548d48842b7b9fa2acd33
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05744480

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