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

HRID 1776025Notes

Reaction equation

HRID 1776025 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-f045d3a9eb774e919dd2222e64f2203e
Source dataset
uspto-grants-2016_02
Patent number
US09260414B2

Reaction notes

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