4-(Dimethylamino)Benzaldehyde → 3-Bromo-4-(dimethylamino)benzaldehyde

HRID 1790193Notes

Reaction equation

HRID 1790193 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[Br-:12].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[Br:12][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[N:2]([CH3:11])[CH3:1])[CH:7]=[O:8]

Participants

4

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 21124087Pyridiniumtribromide

Product 1

HCID 986413-Bromo-4-(dimethylamino)benzaldehydeYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(dimethylamino)-benzaldehyde (10.0 g, 67.03 mmol) in dichloromethane (250 mL) was added pyridinium tribromide (21.4 g, 67.03 mmol). The reaction mixture was stirred at room temperature overnight. The solution was washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. Chromatography on silica gel (15% EtOAc in hexane) afforded 14.06 g of 3-bromo-4-(dimethylamino)-benzaldehyde (92%).

Workup

  1. washThe solution was washed successively with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-ecb4f7b1ddfc45b2a209c0bd72c64a72
Source dataset
uspto-grants-2006_07
Patent number
US07071218B2

Reaction notes

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