1-(2,4,6-Tris(1-methylethyl)phenyl)ethan-1-one → HCID 15725271, compound

HRID 1843746Notes

Reaction equation

HRID 1843746 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[C:16](=[O:18])[CH3:17])([CH3:3])[CH3:2].[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:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][C:8]([CH:10]([CH3:11])[CH3:12])=[CH:7][C:6]=1[CH:13]([CH3:15])[CH3:14])=[O:18]

Participants

4

Reactant 2

HCID 752241-(2,4,6-Tris(1-methylethyl)phenyl)ethan-1-oneHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 15725271HCID 15725271, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(2,4,6-triisopropylphenyl)ethanone (10.0 g, 65.3 mmol) in acetonitrile (81 mL) was added tetrabutylammoniumtribromide (TBABr3, 19.6 g, 40.6 mmol). The reaction was stirred at room temperature for 3.0 h. 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-(2,4,6-triisopropylphenyl)ethanone (13.2 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-5f24fc7ea3d648a5995105c91338c03f
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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