Water → 2-Bromo-1-[3-methoxy-5-(pentafluorosulfanyl)phenyl]ethanone

HRID 657933노트

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HRID 657933 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15](=[O:17])[CH3:16])[CH:6]=[C:7]([S:9]([F:14])([F:13])([F:12])([F:11])[F:10])[CH:8]=1.[Br-:18].[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.O.C(=O)([O-])O.[Na+]>C1COCC1>[Br:18][CH2:16][C:15]([C:5]1[CH:6]=[C:7]([S:9]([F:10])([F:11])([F:12])([F:13])[F:14])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:17]

참가 물질

6

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 441831181-[3-Methoxy-5-(pentafluorosulfanyl)phenyl]ethanone

생성물 1

HCID 581368352-Bromo-1-[3-methoxy-5-(pentafluorosulfanyl)phenyl]ethanone수율 105.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1-[3-Methoxy-5-(pentafluorosulfanyl)phenyl]ethanone (O2.007; 1.63 g) was dissolved in THF (150 ml), and phenyltrimethylammonium tribromide (2.2 g) was added at RT while stirring. After stirring at RT for 2 h, the mixture was admixed with water, neutralized with sodium hydrogencarbonate solution and extracted three times with EA. The alkaline water phase was extracted 3× with EA. The combined organic phases were dried over magnesium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. The residue was purified by means of preparative HPLC (met. A). The product fractions, each of them clean, were combined, freed of the acetonitrile under reduced pressure, neutralized with sodium hydrogencarbonate and extracted three times with EA. The combined organic phases were dried over magnesium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. 1.27 g of the title compound were isolated. LC-MS rt: 1.65 min [M+H]+: 354.9 (met. b)

후처리

  1. stirringAfter stirring at RT for 2 h
  2. extractionextracted three times with EA
  3. extractionThe alkaline water phase was extracted 3× with EA
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationafter the desiccant had been filtered off
  6. customdried under reduced pressure
  7. customThe residue was purified by means of preparative HPLC (
  8. extractionextracted three times with EA
  9. dry with materialThe combined organic phases were dried over magnesium sulfate
  10. filtrationafter the desiccant had been filtered off
  11. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-a182683439954b659a3903f23235cf08
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076336B2

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