Potassium Carbonate → HCID 86625157, compound

HRID 1663359Notes

Reaction equation

HRID 1663359 reaction equation
[Br:1][C:2]1[C:3]([OH:11])=[C:4]([OH:10])[CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17]Br.[C:22](=[O:25])([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.O>[Br:1][C:2]1[CH:9]=[C:6]([CH:5]=[C:4]([O:10][CH2:7][C:6]2[CH:9]=[CH:2][CH:3]=[C:4]([O:25][CH3:22])[CH:5]=2)[C:3]=1[O:11][CH2:17][C:16]1[CH:19]=[CH:20][CH:21]=[C:14]([O:13][CH3:12])[CH:15]=1)[CH:7]=[O:8]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 854055-Bromo-3,4-dihydroxybenzaldehydeHCID 40672073-Methoxybenzyl bromide

Product 1

HCID 86625157HCID 86625157, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-bromo-3,4-dihydroxybenzaldehyde (100 mg), 3-methoxybenzyl bromide (71 μl), potassium carbonate (140 mg) and tetrabutylammonium iodide (10 mg) in 5 ml of DMF was stirred at 60° C. for 3 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eecf3d687907452d9db9fb5d7b331a64
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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