1-(4-Bromo-3-methylphenyl)ethanone → 2-Bromo-1-(4-bromo-3-methylphenyl)ethanone

HRID 1411343Notes

Reaction equation

HRID 1411343 reaction equation
[Br-:1].[Br-].[Br-].C[N+](C)(C)C1C=CC=CC=1.C[N+](C1C=CC=CC=1)(C)C.C[N+](C1C=CC=CC=1)(C)C.[Br:34][C:35]1[CH:40]=[CH:39][C:38]([C:41](=[O:43])[CH3:42])=[CH:37][C:36]=1[CH3:44]>C1COCC1>[Br:1][CH2:42][C:41]([C:38]1[CH:39]=[CH:40][C:35]([Br:34])=[C:36]([CH3:44])[CH:37]=1)=[O:43]

Participants

4

Reactant 2

HCID 3471241-(4-Bromo-3-methylphenyl)ethanoneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 591663462-Bromo-1-(4-bromo-3-methylphenyl)ethanoneYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trimethyl phenylammonium tribromide (13 g, 0.036 mol) was added to a solution of 1-(4-bromo-3-methyl-phenyl)-ethanone (6.3 g, 0.030 mol) in THF (30 mL) and the reaction mixture was stirred at RT for 12 h, filtered, and concentrated to provide the title intermediate (8.6 g, 100% yield). 1H NMR (CDCl3, 400 MHz) δ (ppm): 7.82 (m, 1H), 7.66 (m, 2H), 4.38 (s, 2H), 2.56 (s, 3H)

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7319e3f7c10a44148aa65823923fbbd4
Source dataset
uspto-grants-2014_12
Patent number
US08921372B2

Reaction notes

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