Tetra-n-butylammonium tribromide → HCID 58442385, compound

HRID 1480658Notes

Reaction equation

HRID 1480658 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([C:11](=[O:13])[CH3:12])=[C:6]([CH3:14])[CH:5]=1)[CH3:2].[Br-:15].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C>[Br:15][CH2:12][C:11]([C:7]1[C:8]([CH3:10])=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]=1[CH3:14])=[O:13]

Participants

4

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromideHCID 58442379HCID 58442379, compound

Product 1

HCID 58442385HCID 58442385, compoundYield 113.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(4-ethoxy-2,6-dimethylphenyl)ethanone (4.00 g, 20.8 mmol) in acetonitrile (41.6 mL) was added tetrabutylammoniumtribromide (TBABr3, 10.0 g, 20.8 mmol). The reaction was stirred at room temperature overnight. The solution was concentrated under reduced pressure, added with water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4(s), and concentrated under reduced pressure to give 2-bromo-1-(4-ethoxy-2,6-dimethylphenyl)ethanone (6.40 g), which was used directly for the next step without further purification.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionadded with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous MgSO4(s)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-150026e589144d86ab6d5c57680e5010
Source dataset
uspto-grants-2016_08
Patent number
US09409902B2

Reaction notes

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