Tetra-n-butylammonium tribromide → HCID 58442421, compound

HRID 1843801Notes

Reaction equation

HRID 1843801 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH: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-:20].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C>[Br:19][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]2[CH:5]=[C:4]([CH3:15])[C:3]([C:16](=[O:18])[CH2:17][Br:20])=[C:2]([CH3:1])[CH:7]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromideHCID 58442420HCID 58442420, compound

Product 1

HCID 58442421HCID 58442421, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(2,6-dimethyl-4-(phenylamino)phenyl)ethanone (2.10 g, 8.78 mmol) in acetonitrile (50 mL) was added tetrabutylammoniumtribromide (TBABr3, 4.24 g, 8.78 mmol). The reaction was stirred at room temperature for 60 min. 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 1-(4-(4-bromophenylamino)-2,6-dimethylphenyl)-2-bromoethanone (2.01 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-dc3b6a8a61364c93bdedc20288bdbb57
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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