Water → HCID 58045907, compound

HRID 657949Notes

Reaction equation

HRID 657949 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:15](=[O:17])[CH3:16])[CH:8]=[C:9]([O:11][CH2:12][CH2:13][F:14])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br-:18].[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>CO.C1COCC1>[Br:18][CH2:16][C:15]([C:7]1[CH:8]=[C:9]([O:11][CH2:12][CH2:13][F:14])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 58045918HCID 58045918, compound

Product 1

HCID 58045907HCID 58045907, compoundYield 120.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1-[3-tert-Butyl-5-(2-fluoroethoxy)phenyl]ethanone (O2.105; 600 mg) was dissolved in methanol/THF (15/15 ml). While stirring, phenyltrimethylammonium tribromide (950 mg) was added. After stirring at RT for 3 h, water (5 ml) was added and the mixture was dried. The residue was admixed with DCM (200 ml) and saturated sodium hydrogencarbonate solution (100 ml). The DCM phase was removed and the aqueous phase was extracted three times more with DCM. The combined DCM phases were dried over sodium sulfate, filtered and concentrated. The residue was purified using silica gel (50 g cartridge, n-heptane/EA gradient of 0-60% within 40 min). 560 mg of the title compound were obtained.

Workup

  1. stirringAfter stirring at RT for 3 h
  2. customthe mixture was dried
  3. customThe DCM phase was removed
  4. extractionthe aqueous phase was extracted three times more with DCM
  5. dry with materialThe combined DCM phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified
  9. customsilica gel (50 g cartridge, n-heptane/EA gradient of 0-60% within 40 min)

Sources & evidence

ORD record
ord-28c24e5afc17457189a60d1996447f08
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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