Ethyl bromoacetate → 4(4-Fluorobenzoyl)-2,3-dichlorophenoxy acetic acid

HRID 1862803노트

반응식

HRID 1862803 반응식
[Na].[F:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([Cl:16])[C:10]=2[Cl:17])=[O:8])=[CH:5][CH:4]=1.Br[CH2:21][C:22]([O:24]CC)=[O:23].[OH-].[Na+]>C(O)C>[F:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:21][C:22]([OH:24])=[O:23])=[C:11]([Cl:16])[C:10]=2[Cl:17])=[O:8])=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 130157072,3-Dichloro-4-hydroxy-4'-fluorobenzophenone

생성물 1

HCID 203936894(4-Fluorobenzoyl)-2,3-dichlorophenoxy acetic acid

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

Into a solution of 1.4 g. (0.06 g. atom) of sodium in 200 ml. of absolute alcohol, 16.0 g. (0.056 mole) of 4(4-fluorobenzoyl)-2,3-dichlorophenol was added and the mixture was stirred for thirty minutes at room temperature. The excess of alcohol was vacuum removed and the residue was washed with ether to obtain the sodium salt. The sodium salt of 4(4-fluorobenzoyl)-2,3-dichlorophenol was dissolved in 200 ml. of ethanol and 10.5 g. (0.06 mole) of ethyl bromoacetate was added and the reaction mixture was refluxed for 16 hours, filtered and the solvent was removed in vacuo. The residue was triturated with pet. ether and filtered to obtain a solid product. The product obtained was dissolved in 150 ml. ethanol and 50 ml. of 20% NaOH aqueous solution was added. The reaction mixture was refluxed for 1/2 hour and the solvent was partially removed in vacuo. The residue was dissolved in hot water and filtered. The hot filtrate was acidified with concentrated hydrochloric acid at 60° C. The resulting precipitate was collected by filtration and washed with water. Recrystallization from dichloroethane afforded 8.0 g. (47%) of the product; m.p. 174°-176°.

후처리

  1. temperaturethe reaction mixture was refluxed for 16 hours
  2. filtrationfiltered
  3. customthe solvent was removed in vacuo
  4. customThe residue was triturated with pet. ether
  5. filtrationfiltered
  6. customto obtain a solid product
  7. customThe product obtained
  8. dissolutionwas dissolved in 150 ml
  9. temperatureThe reaction mixture was refluxed for 1/2 hour
  10. customthe solvent was partially removed in vacuo
  11. dissolutionThe residue was dissolved in hot water
  12. filtrationfiltered
  13. customwas acidified with concentrated hydrochloric acid at 60° C
  14. filtrationThe resulting precipitate was collected by filtration
  15. washwashed with water
  16. customRecrystallization from dichloroethane
  17. customafforded 8.0 g

출처 및 근거

ORD 기록
ord-c1e4f7df93a147b28030758e0e76281b
출처 데이터셋
uspto-grants-1979_09
특허 번호
US04166819

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