Tetra-n-butylammonium tribromide → HCID 58442436, compound

HRID 1480671Notes

Reaction equation

HRID 1480671 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[C:4]([CH3:15])[C:3]=1[C:16](=[O:18])[CH3:17].[Br-:19].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C>[Br:19][CH2:17][C:16]([C:3]1[C:4]([CH3:15])=[CH:5][C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][C:2]=1[CH3:1])=[O:18]

Participants

4

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromideHCID 58442556HCID 58442556, compound

Product 1

HCID 58442436HCID 58442436, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(2,6-dimethyl-4-phenoxyphenyl)ethanone (3.60 g, 15.0 mmol) in acetonitrile (30 mL) was added tetrabutylammoniumtribromide (TBABr3, 7.95 g, 15.0 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-(2,6-dimethyl-4-phenoxyphenyl)ethanone (4.8 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-70a3e1f77fe24c199601ec5e0b449b4c
Source dataset
uspto-grants-2016_08
Patent number
US09409902B2

Reaction notes

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