Potassium Carbonate → HCID 60628022, compound

HRID 1686145Notes

Reaction equation

HRID 1686145 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH2:12]Br)=[C:6]([CH:9]=1)[CH:7]=[O:8].C([O-])([O-])=O.[K+].[K+].[Br:20][C:21]1[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH2:12][O:27][C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([Br:20])[CH:22]=2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 17620916HCID 17620916, compound

Product 1

HCID 60628022HCID 60628022, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-2-(2-bromoethoxy)benzaldehyde (170 mg, 0.55 mol) obtained in step 1) was dissolved in DMF (20 ml), and K2CO3 (229.43 mg, 1.66 mmol), KI (9.96 mg, 0.06 mmol), and 3-bromophenol (95.46 mg, 0.55 mmol) were added to the solution, followed by stirring for 2 hours at an elevated temperature. After completion of the reaction, the reaction solution was cooled to room temperature, washed with an aqueous saturated NH4Cl solution and extracted with ethyl acetate. The organic layer thus obtained was washed one more time with an aqueous saturated NH4Cl solution. Then, the organic layer was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo. The residue was subjected to column chromatography (ethyl acetate/n-hexane=1/9) to afford the object compound (pale yellowish solid, 161 mg, 72.7%).

Workup

  1. customAfter completion of the reaction
  2. washwashed with an aqueous saturated NH4Cl solution
  3. extractionextracted with ethyl acetate
  4. customThe organic layer thus obtained
  5. washwas washed one more time with an aqueous saturated NH4Cl solution
  6. dry with materialThen, the organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto afford the object compound (pale yellowish solid, 161 mg, 72.7%)

Sources & evidence

ORD record
ord-84de521ee3bc4258855dd5a130833f42
Source dataset
uspto-grants-2012_04
Patent number
US08148541B2

Reaction notes

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