Potassium Iodide → 5-(2-Propyl-3,4-dichlorophenoxy)pentyl bromide

HRID 34969

반응식

HRID 34969 반응식
[CH2:1]([C:4]1[C:9]([Cl:10])=[C:8]([Cl:11])[CH:7]=[CH:6][C:5]=1[OH:12])[CH2:2][CH3:3].[H-].[Na+].[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br.[I-].[K+]>O.C(OCC)(=O)C.CN(C)P(N(C)C)(N(C)C)=O.O1CCCC1>[CH2:1]([C:4]1[C:9]([Cl:10])=[C:8]([Cl:11])[CH:7]=[CH:6][C:5]=1[O:12][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][Br:15])[CH2:2][CH3:3]

참가 물질

9

반응물 4

HCID 4875Potassium IodideHCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 6003603,4-Dichloro-2-propylphenol

생성물 1

HCID 212972695-(2-Propyl-3,4-dichlorophenoxy)pentyl bromide

시약·촉매·용매 4

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 12679Hexamethylphosphoramide용매

실험 절차

To a solution of 3.12 g. of 2-propyl-3,4dichlorophenol in 30 ml. of dry tetrahydrofuran and 30 ml. of dry hexamethylphosphoramide were added 0.72 g. of a 50% sodium hydride dispersion in oil. Two milliliters of 1,5-dibromopentane were then added followed by a catalytic amount of potassium iodide. The reaction was stirred overnight under a nitrogen atmosphere at 60°-70° C. The reaction was then cooled to room temperature, ethyl acetate and water were added, and the solution was evaporated to dryness. Ethyl acetate and water were added to the residue and the layers were separated. The ethyl acetate layer was washed with dilute acid to remove residual hexamethylphosphoramide. The ethyl acetate was then washed with a saturated sodium chloride solution, filtered through sodium sulfate, and evaporated to dryness. The residue was purified by high pressure liquid chromatography to provide 1.6 g. of the desired bromo intermediate. NMR.

후처리

  1. customthe solution was evaporated to dryness
  2. additionEthyl acetate and water were added to the residue
  3. customthe layers were separated
  4. washThe ethyl acetate layer was washed
  5. additionwith dilute acid
  6. customto remove residual hexamethylphosphoramide
  7. washThe ethyl acetate was then washed with a saturated sodium chloride solution
  8. filtrationfiltered through sodium sulfate
  9. customevaporated to dryness
  10. customThe residue was purified by high pressure liquid chromatography
  11. customto provide 1.6 g

출처 및 근거

ORD 기록
ord-32c6fb647d2746f4aba904176db85cf6
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04764521

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