Water → HCID 22121436, compound

HRID 657937Notes

Reaction equation

HRID 657937 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[Br-:13].[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.CC(=O)OCC>CO.C1COCC1>[Br:13][CH2:11][C:10]([C:4]1[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=[C:2]([Br:1])[CH:3]=1)=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 197023411-(3-Bromo-5-methoxyphenyl)ethan-1-one

Product 1

HCID 22121436HCID 22121436, compoundYield 123%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1-(3-Bromo-5-methoxyphenyl)ethanone (O2.032, 1.45 g) was dissolved in methanol/THF (40 ml/40 ml) and admixed while stirring with phenyltrimethylammonium tribromide (2.38 g). After stirring at RT for 24 h, water and EA were added. The EA phase was removed, dried and concentrated. The residue was dissolved in acetonitrile (50 ml), and 2 N sulfuric acid (15 ml) was added to the solution. After standing at RT for 1 h, the mixture was admixed with water and extracted twice with EA. The EA phase was washed with saturated sodium hydrogencarbonate solution, dried and concentrated. The residue was purified using silica gel (40 g cartridge, n-heptane/EA gradient of 0-50% within 30 min). 1.39 g of the title compound were obtained.

Workup

  1. customThe EA phase was removed
  2. customdried
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in acetonitrile (50 ml)
  5. addition2 N sulfuric acid (15 ml) was added to the solution
  6. waitAfter standing at RT for 1 h
  7. extractionextracted twice with EA
  8. washThe EA phase was washed with saturated sodium hydrogencarbonate solution
  9. customdried
  10. concentrationconcentrated
  11. customThe residue was purified
  12. customsilica gel (40 g cartridge, n-heptane/EA gradient of 0-50% within 30 min)

Sources & evidence

ORD record
ord-448fd36e603f46b9b265659b7d6188eb
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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