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

HRID 657933Notes

Reaction equation

HRID 657933 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-a182683439954b659a3903f23235cf08
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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