Water → 5-Bromo-2-(3,4-dichlorophenoxy)benzaldehyde

HRID 1454224Notes

Reaction equation

HRID 1454224 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].C([O-])([O-])=O.[K+].[K+].[Cl:17][C:18]1[CH:19]=[C:20]([OH:25])[CH:21]=[CH:22][C:23]=1[Cl:24].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][C:20]2[CH:21]=[CH:22][C:23]([Cl:24])=[C:18]([Cl:17])[CH:19]=2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 120170305-Bromo-2-(3,4-dichlorophenoxy)benzaldehydeYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-bromo-2-fluoro-benzaldehyde (5.13 g, 25.4 mmol) in DMF (25 mL) were added K2CO3 (7.15 g, 51.8 mmol) and 3,4-dichloro-phenol (4.67 g, 28.8 mmol). The mixture was heated at 90° C. for 24 h and then was allowed to cool to room temperature (rt). Water was added and the mixture was extracted with Et2O. The combined organic layers were dried (MgSO4) and concentrated. The residue was diluted with DCM and hexanes and the resulting solids were collected by vacuum filtration to provide the desired product (4.74 g, 54%). 1H NMR (CDCl3): 10.36 (s, 1H), 8.06 (d, J=2.5, 1H), 7.67 (dd, J=8.8, 2.6, 1H), 7.46 (d, J=8.8, 1H), 7.17 (d, J=2.8, 1H), 6.92 (dd, J=8.8, 2.8, 1H), 6.84 (d, J=8.8, 1H).

Workup

  1. temperatureto cool to room temperature (rt)
  2. extractionthe mixture was extracted with Et2O
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. additionThe residue was diluted with DCM and hexanes
  6. filtrationthe resulting solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-c2123d84604242fc8d6495a7e20bed67
Source dataset
uspto-grants-2009_01
Patent number
US07479493B2

Reaction notes

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