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

HRID 217709Notes

Reaction equation

HRID 217709 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([N:17](C)[C:18](=O)C(F)(F)F)[CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)=[O:4].O.S(=O)(=O)(O)O.[OH-].[Na+]>CC(=O)OCC>[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[C:9]([S:11]([F:16])([F:12])([F:13])([F:14])[F:15])[CH:8]=[C:7]([NH:17][CH3:18])[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 58136859HCID 58136859, compound

Product 1

HCID 452578932-Bromo-1-[3-methylamino-5-(pentafluorosulfanyl)phenyl]ethanoneYield 44.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

N-[3-(2-Bromoacetyl)-5-(pentafluoro sulfanyl)phenyl]-2,2,2-trifluoro-N-methylacetamide (O1.075; 1.2 g) was admixed with water (15 ml), and concentrated sulfuric acid (15 ml) was added dropwise while stirring and with ice cooling. The mixture was heated to 80° C. and stirred at this temperature for 7 h. After cooling, the reaction mixture was added slowly to a mixture of 10 N sodium hydroxide solution and EA, and the aqueous phase was extracted five times 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. 420 mg of the title compound were isolated.

Workup

  1. additionwas added dropwise
  2. stirringstirred at this temperature for 7 h
  3. temperatureAfter cooling
  4. extractionthe aqueous phase was extracted five times with EA
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. filtrationafter the desiccant had been filtered off
  7. customdried under reduced pressure
  8. customThe residue was purified by means of preparative HPLC (
  9. extractionextracted three times with EA
  10. dry with materialThe combined organic phases were dried over magnesium sulfate
  11. filtrationafter the desiccant had been filtered off
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-8f8915b7ff364463b678b06ec4fe6dab
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Reaction notes

Loading…