Phenyltrimethylammonium bromide dibromide → 2-Bromo-1-(4-bromo-2-methylphenyl)ethanone

HRID 520346Notes

Reaction equation

HRID 520346 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([CH3:11])[CH:3]=1.[Br-:12].[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>C1COCC1>[Br:12][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[CH3:11])=[O:10]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 219385361-(4-Bromo-2-methylphenyl)ethan-1-one

Product 1

HCID 126225062-Bromo-1-(4-bromo-2-methylphenyl)ethanoneYield 84.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-bromo-2-methylphenyl)ethanone (0.525 g, 2.464 mmol) in THF was added phenyltrimethylammonium tribromide (0.926 g, 2.464 mmol). The reaction mixture was stirred at rt for 16 hrs. The reaction mixture was filtered through a plug of diatomaceous earth (Celite®), and the filtrate was concentrated to yield 2-bromo-1-(4-bromo-2-methylphenyl)-ethanone (0.61 g) as a white solid. LC/MS (Cond. N-1): [M+H]+ 290.84, Rt=3.88 min.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of diatomaceous earth (Celite®)
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2eb17bfbea9e48c7a7405678ca258b86
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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