4-Hydroxybenzaldehyde → 4-[(3,5-Dichloro-4-pyridinyl)methoxy]benzaldehyde

HRID 991558Notes

Reaction equation

HRID 991558 reaction equation
Br[CH2:2][C:3]1[C:8]([Cl:9])=[CH:7][N:6]=[CH:5][C:4]=1[Cl:10].[OH:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Cl:10][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:9])[C:3]=1[CH2:2][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 10796Cesium carbonateHCID 222277664-(Bromomethyl)-3,5-dichloropyridine

Product 1

HCID 184140224-[(3,5-Dichloro-4-pyridinyl)methoxy]benzaldehydeYield 91.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(bromomethyl)-3,5-dichloropyridine (15 g, 62.2 mmol), 4-hydroxybenzaldehyde (7.97 g, 65.4 mmol) and caesium carbonate (22.3 g, 68.5 mmol) in DMF (150 ml) was stirred for 4.5 h at room temperature. The mixture was poured into water and extracted with EtOAc. The organic extract was washed with sodium carbonate solution (×2) and brine, dried (MgSO4) and evaporated in vacuo to give the title compound as a brown solid (16 g). δH (DMSO-d6), 9.91 (1H, s), 8.74 (2H, s), 7.91 (2H, d, J 8.6 Hz), 7.27 (2H, d, J 8.6 Hz), 5.37 (2H, s); m/z (ESI) 282 (MH+).

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with sodium carbonate solution (×2) and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-24ff024a49ed44b9b3044029b9c4798e
Source dataset
uspto-grants-2002_10
Patent number
US06465471B1

Reaction notes

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