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Acetic Anhydride → 3,4,5-Tribromopyrazole-1-ethanol acetate

HRID 372197
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HRID 372197 반응식
[Br:1][C:2]1[C:6]([Br:7])=[C:5]([Br:8])[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:15]([O:18][CH2:19][CH2:20]Br)(=[O:17])[CH3:16].C(OC(=O)C)(=O)C>CC(C)=O>[C:15]([O:18][CH2:19][CH2:20][N:3]1[C:2]([Br:1])=[C:6]([Br:7])[C:5]([Br:8])=[N:4]1)(=[O:17])[CH3:16]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 6276743,4,5-tribromo-1H-pyrazole

생성물 1

HCID 537332873,4,5-Tribromopyrazole-1-ethanol acetate

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A quantity (3.04 g., 0.01 mole) of 3,4,5-tribromopyrazole was dissolved in 70 ml. acetone and 2.76 g. (0.02 mole) solid anhydrous potassium carbonate was added. The mixture was heated at the reflux temperature with stirring for 10 minutes and after cooling, 1.85 g. (0.011 mole) of 2-bromoethyl acetate was added. This reaction mixture was heated at the reflux temperature for 12 hrs. cooled, filtered, and the acetone removed under reduced pressure. The resultant oil consisted of a mixture of the desired acetate and the corresponding alcohol. The mixture was dissolved in pyridine (15 ml.) and treated with acetic anhydride (3.06 g., 0.03 mole) at 0° C. This reaction mixture was kept at about 25° C. overnight, and then poured into 200 ml. of ice water. The precipitate that formed was collected on a filter, and washed with water. After drying and recrystallizing from hexane there was obtained 3,4,5-tribromopyrazole-1-ethanol acetate (ester) having a melting point at 64° to 67° C.

후처리

  1. temperatureThe mixture was heated at the reflux temperature
  2. temperatureafter cooling
  3. temperatureThis reaction mixture was heated at the reflux temperature for 12 hrs
  4. temperaturecooled
  5. filtrationfiltered
  6. customthe acetone removed under reduced pressure
  7. additionThe resultant oil consisted of a mixture of the desired acetate
  8. dissolutionThe mixture was dissolved in pyridine (15 ml.)
  9. waitThis reaction mixture was kept at about 25° C. overnight
  10. additionpoured into 200 ml
  11. customThe precipitate that formed
  12. customwas collected on a filter
  13. washwashed with water
  14. customAfter drying
  15. customrecrystallizing from hexane

출처 및 근거

ORD 기록
ord-837396d8a56e43589b09acd1e43b9518
출처 데이터셋
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04089672

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