Citric Acid → 2-Bromo-1-[3-morpholin-4-yl-5-(pentafluorosulfanyl)phenyl]ethanone

HRID 1258530Notes

Reaction equation

HRID 1258530 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([C:19](=[O:21])[CH3:20])[CH:10]=[C:11]([S:13]([F:18])([F:17])([F:16])([F:15])[F:14])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br-:22].[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.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(Cl)Cl>CO.C1COCC1>[Br:22][CH2:20][C:19]([C:9]1[CH:10]=[C:11]([S:13]([F:15])([F:14])([F:16])([F:17])[F:18])[CH:12]=[C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH:8]=1)=[O:21]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6344DichloromethaneHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 581367861-[3-Morpholin-4-yl-5-(pentafluorosulfanyl)phenyl]ethanone

Product 1

HCID 581369122-Bromo-1-[3-morpholin-4-yl-5-(pentafluorosulfanyl)phenyl]ethanoneYield 109.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1-[3-Morpholin-4-yl-5-(pentafluorosulfanyl)phenyl]ethanone (1.1 g) was dissolved in methanol/THF (20/20 ml), and phenyltrimethylammonium tribromide (1.25 g) was added while stirring. After stirring at RT for 27 h, 20% citric acid (50 ml) was added and the mixture was stirred for 1 h. After adding DCM (100 ml), the DCM phase was removed, dried and concentrated. The residue was dissolved in acetonitrile (100 ml), and 2N sulfuric acid (20 ml) was added to the solution. After stirring at RT for 24 h, water was added and the mixture was extracted with EA. The EA phase was washed with saturated sodium hydrogencarbonate solution, dried and concentrated. The residue was purified using silica gel (80 g cartridge, n-heptane/EA gradient of 0-60% within 40 min). 866 mg of the title compound were obtained.

Workup

  1. stirringAfter stirring at RT for 27 h
  2. stirringthe mixture was stirred for 1 h
  3. customthe DCM phase was removed
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in acetonitrile (100 ml)
  7. addition2N sulfuric acid (20 ml) was added to the solution
  8. stirringAfter stirring at RT for 24 h
  9. additionwater was added
  10. extractionthe mixture was extracted with EA
  11. washThe EA phase was washed with saturated sodium hydrogencarbonate solution
  12. customdried
  13. concentrationconcentrated
  14. customThe residue was purified
  15. customsilica gel (80 g cartridge, n-heptane/EA gradient of 0-60% within 40 min)

Sources & evidence

ORD record
ord-7c09da0d23364696bf2402257e31a32f
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

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