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

HRID 2212585Notes

Reaction equation

HRID 2212585 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 g, 67.03 mmol) in dichloromethane (250 mL) was added pyridinium tribromide (21.4 g, 67.03 mmol) and the reaction mixture stirred at room temperature overnight. The solution was washed with water and brine, dried (MgSO4), filtered and evaporated. The residue was purified on silica gel (eluent: 15% ethyl acetate in hexane) to give 14.06 g of 3-bromo-4-dimethylamino-benzaldehyde (92%). 1H NMR (300 MHz; CDCl3): δ 2.59 (s, 6 H), 7.06 (d, J=8.1 Hz, 1 H), 7.75 (dd, J=7.8 Hz and 1.5 Hz, 1 H), 5.74 (s, 1 H), 7.06 (d, J=8.1 Hz, 1 H), 7.43 (dd, J=2.1 Hz and 8.4 Hz, 1 H), 8.04 (d, J=1.8 Hz, 1 H), 9.81 (s, 1 H).

Workup

  1. washThe solution was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified on silica gel (eluent: 15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-abd0be44ef204d56967b9246539392d8
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

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