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

HRID 1358382Notes

Reaction equation

HRID 1358382 reaction equation
C([O-])([O-])=O.[K+].[K+].[Cl:7][C:8]1[CH:9]=[C:10]([OH:15])[CH:11]=[CH:12][C:13]=1[Cl:14].[Br:16][C:17]1[CH:18]=[CH:19][C:20](F)=[C:21]([CH:24]=1)[CH:22]=[O:23]>CN(C)C=O>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([O:15][C:10]2[CH:11]=[CH:12][C:13]([Cl:14])=[C:8]([Cl:7])[CH:9]=2)=[C:21]([CH:24]=1)[CH:22]=[O:23]

Participants

5

Reactant 3

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

Product 1

HCID 120170305-Bromo-2-(3,4-dichlorophenoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
95 °C

Procedure

Under N2 in a 1 L round-bottomed flask fitted with a reflux condenser and magnetic stirrer were placed 51.1 g (370 mmol) of K2CO3 and 20.1 g (123 mmol) of 3,4-dichlorophenol (Aldrich Chem. Co., Milwaukee, Wis.) in 500 mL of anhydrous N,N-dimethylformamide (DMF). After stirring the mixture for 30 min., 25 g (123 mmol) of 5-bromo-2-fluoro-benzaldehyde (Aldrich) in 150 mL of DMF was added and the mixture was heated to 90-100° C. overnight. After allowing the reaction to cool to room temperature, the mixture was concentrated at reduced pressure on a rotary evaporator and the resulting oily residue was then diluted with water and EtOAc. The aqueous layer was then extracted with additional EtOAc and the organic layers were combined, washed with H2O and saturated NaCl and dried over Na2SO4. Removal of the solvent in vacuo gave a light yellow oil which was further dried under vacuum overnight to give the title product as a pale yellow solid, 40.2 g; m.p. 129-132° C.

Workup

  1. customUnder N2 in a 1 L round-bottomed flask fitted with a reflux condenser and magnetic stirrer
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. concentrationthe mixture was concentrated at reduced pressure on a rotary evaporator
  5. additionthe resulting oily residue was then diluted with water and EtOAc
  6. extractionThe aqueous layer was then extracted with additional EtOAc
  7. washwashed with H2O and saturated NaCl
  8. dry with materialdried over Na2SO4
  9. customRemoval of the solvent in vacuo
  10. customgave a light yellow oil which
  11. customwas further dried under vacuum overnight

Sources & evidence

ORD record
ord-f392a558180544d2a948e6d6828e37de
Source dataset
uspto-grants-2003_07
Patent number
US06596741B2

Reaction notes

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