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

HRID 217718ノート

反応式

HRID 217718 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f42d59efb6344e459909d61e57427466
出典データセット
uspto-grants-2012_06
特許番号
US08198272B2

反応ノート

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