Benzene → 3-Acetyl-5-(4-(4-bromo-2-fluorophenoxy)phenoxy)-2,4-hexanedione

HRID 4464

반응식

HRID 4464 반응식
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].C1C=CC=CC=1.[Na].[Br:15][C:16]1[CH:34]=[CH:33][C:19]([O:20][C:21]2[CH:32]=[CH:31][C:24]([O:25][CH:26]([CH3:30])[C:27](Cl)=[O:28])=[CH:23][CH:22]=2)=[C:18]([F:35])[CH:17]=1>CCOCC.O>[C:4]([CH:3]([C:27](=[O:28])[CH:26]([O:25][C:24]1[CH:31]=[CH:32][C:21]([O:20][C:19]2[CH:33]=[CH:34][C:16]([Br:15])=[CH:17][C:18]=2[F:35])=[CH:22][CH:23]=1)[CH3:30])[C:2](=[O:7])[CH3:1])(=[O:6])[CH3:5]

참가 물질

7

반응물 4

HCID 241BenzeneHCID 31261AcetylacetoneHCID 5360545SodiumHCID 143726022-(4-(4-Bromo-2-fluorophenoxy)phenoxy)propanoyl chloride

생성물 1

HCID 201525943-Acetyl-5-(4-(4-bromo-2-fluorophenoxy)phenoxy)-2,4-hexanedione수율 16%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

A mixture of 1.7 g (17 mmol) of 2,4-pentanedione, 30 ml of benzene and 0.26 g (11.3 mmol) of sodium was warmed at reflux for 3 hours. The reaction mixture was cooled to room temperature and a solution of 10 mmol of 2-(4-(4-bromo-2-fluorophenoxy)phenoxy)propanoyl chloride was added dropwise. The resulting mixture was warmed at reflux for 2.5 hours, stirred at room temperature overnight and poured into water and ether. The organic layer was separated, dried over MgSO4 and evaporated to dryness. The residue was purified by prep LC, eluting with 4:1 hexane:acetone. The product was taken up in ether and extracted with two portions of 1% aqueous NaOH. The combined aqueous layers were made acidic with aqueous HCl and extracted with ether. The ether layer was evaporated to dryness and the residue again purified by prep LC, eluting with 85:15 hexane:acetone. This gave a yellow oil which was thoroughly dried to leave 0.70 g product. Calc for C20H18BrFO5 : C, 54.93, H, 4.15. Found: C, 54.13, H, 4.30.

후처리

  1. temperaturewas warmed
  2. temperatureat reflux for 3 hours
  3. temperatureThe resulting mixture was warmed
  4. temperatureat reflux for 2.5 hours
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe residue was purified by prep LC
  9. washeluting with 4:1 hexane
  10. extractionextracted with two portions of 1% aqueous NaOH
  11. extractionextracted with ether
  12. customThe ether layer was evaporated to dryness
  13. customthe residue again purified by prep LC
  14. washeluting with 85:15 hexane
  15. customThis gave a yellow oil which
  16. customwas thoroughly dried

출처 및 근거

ORD 기록
ord-0e96676273d2437282408c24a90f4b9f
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725683

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