Potassium Carbonate → 4-(4-Bromo-2-chloro-phenoxy)-benzaldehyde

HRID 1406358Notes

Reaction equation

HRID 1406358 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([Cl:18])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[C:13]([Cl:18])[CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 198594-Bromo-2-chlorophenolHCID 680234-Fluorobenzaldehyde

Product 1

HCID 288931534-(4-Bromo-2-chloro-phenoxy)-benzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 50 mg (0.40 mmol) of 4-fluorobenzaldehyde and 83.6 mg (0.40 mmol) of 4-bromo-2-chlorophenol in 2 mL DMSO was combined with 80 mg (0.58 mmol) of potassium carbonate and stirred overnight at 120° C. The reaction mixture was filtered through Alox B, washed with dichloromethane and evaporated down. The residue was purified by chromatography (reversed phase).

Workup

  1. filtrationThe reaction mixture was filtered through Alox B
  2. washwashed with dichloromethane
  3. customevaporated down
  4. customThe residue was purified by chromatography (reversed phase)

Sources & evidence

ORD record
ord-8ede59f02d5a44f9b08e9bae2d139128
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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