Phenyltrimethylammonium bromide dibromide → 2-Bromo-1-[3-tert-butyl-5-(3-hydroxypropoxy)-4-methoxyphenyl]ethanone

HRID 532367노트

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HRID 532367 반응식
[C:1]([C:5]1[CH:6]=[C:7]([C:24](=[O:26])[CH3:25])[CH:8]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][O:17]C2CCCCO2)[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[Br-:27].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>CO.C1COCC1.C(Cl)Cl>[Br:27][CH2:25][C:24]([C:7]1[CH:8]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][OH:17])[C:10]([O:11][CH3:12])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=1)=[O:26]

참가 물질

5

반응물 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 581367841-{3-tert-Butyl-4-methoxy-5-[3-(tetrahydropyran-2-yloxy)propoxy]phenyl}ethanone

생성물 1

HCID 581369012-Bromo-1-[3-tert-butyl-5-(3-hydroxypropoxy)-4-methoxyphenyl]ethanone수율 45.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

1-{3-tert-Butyl-4-methoxy-5-[3-(tetrahydropyran-2-yloxy)propoxy]phenyl}ethanone (O2.071; 12.7 g) was dissolved in methanol/THF (200/200 ml) and admixed with phenyltrimethylammonium tribromide (13.1 g) while stirring. The mixture was stirred at RT for 1 h, then diluted with DCM and washed once with 5% sodium thiosulfate solution. The DCM phase was dried over magnesium sulfate, filtered and concentrated. The residue was taken up in acetonitrile (100 ml) and admixed with 48% hydrobromic acid (5.91 ml). The mixture was left to stand for 1 h, then admixed with water, extracted by shaking with EA, and the combined EA phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel (120 g cartridge, n-heptane/MtB ether gradient of 0-100% in 60 min). 3.29 g of the title compound were obtained.

후처리

  1. stirringThe mixture was stirred at RT for 1 h
  2. washwashed once with 5% sodium thiosulfate solution
  3. dry with materialThe DCM phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. waitThe mixture was left
  7. extractionextracted
  8. stirringby shaking with EA
  9. dry with materialthe combined EA phases were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified
  13. customsilica gel (120 g cartridge, n-heptane/MtB ether gradient of 0-100% in 60 min)

출처 및 근거

ORD 기록
ord-81ae13c4d9ed426b9232506477bfa997
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853206B2

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