Water → HCID 58136824, compound

HRID 1524536Notes

Reaction equation

HRID 1524536 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:16](=[O:19])[CH2:17][CH3:18])[CH:7]=[C:8]([S:10]([F:15])([F:14])([F:13])([F:12])[F:11])[CH:9]=1)[CH3:2].[Br-:20].[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.CC(=O)OCC>[Br:20][CH:17]([CH3:18])[C:16]([C:6]1[CH:7]=[C:8]([S:10]([F:11])([F:12])([F:13])([F:15])[F:14])[CH:9]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 58136949HCID 58136949, compound

Product 1

HCID 58136824HCID 58136824, compoundYield 109.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[3-Ethoxy-5-(pentafluorosulfanyl)phenyl]propan-1-one (O2.064; 150 mg) was dissolved in THF (15 ml), and phenyltrimethylammonium tribromide (185 mg) was added while stirring at RT. After stirring at RT for 5 h, the mixture was admixed with water and saturated sodium hydrogencarbonate solution, and EA was added. The EA phase was removed and the alkaline water phase was extracted three times with EA. The combined organic phases were washed once with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The crude product 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, alkalized with saturated sodium hydrogencarbonate solution and extracted five times with EA. The combined organic phases were dried over magnesium sulfate and, after filtering off the desiccant, dried under reduced pressure. 120 mg of the title compound were isolated.

Workup

  1. stirringAfter stirring at RT for 5 h
  2. additionwas added
  3. customThe EA phase was removed
  4. extractionthe alkaline water phase was extracted three times with EA
  5. washThe combined organic phases were washed once with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by means of preparative HPLC (
  10. extractionextracted five times with EA
  11. dry with materialThe combined organic phases were dried over magnesium sulfate
  12. filtrationafter filtering off the desiccant,
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-66264f848c6646ceb735576d1f5086dc
Source dataset
uspto-grants-2015_07
Patent number
US09079906B2

Reaction notes

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