3-(Trifluoromethyl)phenol → 3-Chloro-2-(3-(trifluoromethyl)phenoxy)pyridine

HRID 443009

반응식

HRID 443009 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Cl[C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][N:14]=1>CN(C)C=O>[Cl:19][C:18]1[C:13]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)=[N:14][CH:15]=[CH:16][CH:17]=1

참가 물질

4

반응물 2

HCID 73763-(Trifluoromethyl)phenolHCID 169882,3-Dichloropyridine

생성물 1

HCID 180084773-Chloro-2-(3-(trifluoromethyl)phenoxy)pyridine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

7.68 g of sodium hydride dispersion (ca. 50 percent in mineral oil) was washed with pentane under nitrogen and 100 ml of N,N-dimethylformamide was then added. 21.92 g (135 mmol) of 3-(trifluoromethyl)phenol was added dropwise over 30 minutes at room temperature. The resulting phenate solution was added dropwise over 2 hours, under nitrogen, to a solution of 20.1 g (136 mmol) of 2,3-dichloropyridine in 80 ml of N,N-dimethylformamide, heated to 120° C. After 3 hours of reaction time, the mixture was cooled to room temperature, the sodium chloride which had precipitated out was filtered off and the filtrate was concentrated. The residue was extracted with toluene and 0.1N hydrochloric acid and the organic phase was washed with saturated sodium chloride solution and concentrated. The oily residue was distilled under vacuum. The yield was 24.75 g (67 percent) of a colorless oil, content (GC): 99.7 percent. Other data concerning the product was:

후처리

  1. wash7.68 g of sodium hydride dispersion (ca. 50 percent in mineral oil) was washed with pentane under nitrogen
  2. addition100 ml of N,N-dimethylformamide was then added
  3. customAfter 3 hours of reaction time
  4. temperaturethe mixture was cooled to room temperature
  5. customthe sodium chloride which had precipitated out
  6. filtrationwas filtered off
  7. concentrationthe filtrate was concentrated
  8. extractionThe residue was extracted with toluene and 0.1N hydrochloric acid
  9. washthe organic phase was washed with saturated sodium chloride solution
  10. concentrationconcentrated
  11. distillationThe oily residue was distilled under vacuum

출처 및 근거

ORD 기록
ord-b1f797436a324e67b82cf4949508d8ad
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05892032

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