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

HRID 1884504Notes

Reaction equation

HRID 1884504 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. Choromatography 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-0cb6b20980944bfb97fb69d46a19ea5f
Source dataset
uspto-grants-2004_07
Patent number
US06765013B2

Reaction notes

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