3,N-Dimethoxy-N-methyl-5-(pentafluorosulfanyl)benzamide → 1-[3-Methoxy-5-(pentafluorosulfanyl)phenyl]ethanone

HRID 1258517Notes

Reaction equation

HRID 1258517 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[C:13]([S:15]([F:20])([F:19])([F:18])([F:17])[F:16])[CH:14]=1)[C:6](N(OC)C)=[O:7].[CH3:21][Mg]Br>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6](=[O:7])[CH3:21])[CH:12]=[C:13]([S:15]([F:17])([F:20])([F:19])([F:16])[F:18])[CH:14]=1

Participants

4

Reactant 2

HCID 581369683,N-Dimethoxy-N-methyl-5-(pentafluorosulfanyl)benzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 441831181-[3-Methoxy-5-(pentafluorosulfanyl)phenyl]ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,N-Dimethoxy-N-methyl-5-(pentafluorosulfanyl)benzamide (70 mg) was dissolved in absolute THF, and methylmagnesium bromide (185 μl, 2 M in diethyl ether) was added dropwise at 0° C. while stirring. After addition, the ice bath was removed and the mixture was stirred at RT for 2 h. 1N hydrochloric acid was then added dropwise while cooling, followed by water and ethyl acetate. The organic phase was removed and the aqueous phase was extracted twice more with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. The residue was purified by means of preparative HPLC. The product-containing fractions were combined, freed of the acetonitrile and extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 34 mg of the desired compound were obtained.

Workup

  1. additionAfter addition
  2. customthe ice bath was removed
  3. stirringthe mixture was stirred at RT for 2 h
  4. addition1N hydrochloric acid was then added dropwise
  5. temperaturewhile cooling
  6. customThe organic phase was removed
  7. extractionthe aqueous phase was extracted twice more with ethyl acetate
  8. dry with materialThe combined extracts were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by means of preparative HPLC
  12. extractionextracted three times with ethyl acetate
  13. dry with materialThe combined extracts were dried over magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-450c7b2054044f64aed45eba234bb3e9
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

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