Cesium carbonate → HCID 13188736, compound

HRID 844365Notes

Reaction equation

HRID 844365 reaction equation
[Br:1][C:2]1[C:3]([OH:12])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:20][CH2:21][O:22][CH3:23]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[C:6]([CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[O:12][CH2:20][CH2:21][O:22][CH3:23])[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 180995-BromovanillinHCID 809722-Bromoethyl methyl ether

Product 1

HCID 13188736HCID 13188736, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a 500 mL round bottomed flask with a stirring bar, reflux condenser and an argon inlet was added 5-bromovanillin (10 g, 43.28 mmol), DMF (125 mL), powdered Cs2CO3 (28.2 g, 86.56 mmol) and 2-bromoethylmethyl ether (5.08 mL, 54.10 mmol). This well stirred mixture was heated at 75° C. for 24 h. The cooled mixture was filtered through a frit to remove the cesium salts and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc and washed with water and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave an oil. 1H NMR (CDCl3): δ3.44 (s, 3H); 3.77 (t, j=4 Hz, 2H); 3.92 (s, 3H); 4.27 (t, j=4 Hz, 2H); 7.38 (d, j=2 Hz, 1H); 7.65 (d, j=2Hz, 1H); 9.84 (s, 1H).

Workup

  1. temperatureTo a 500 mL round bottomed flask with a stirring bar, reflux condenser and an argon inlet
  2. filtrationThe cooled mixture was filtered through a frit
  3. customto remove the cesium salts
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with water and brine
  7. customDrying
  8. filtration(MgSO4), filtration and removal of the solvent in vacuo
  9. customgave an oil

Sources & evidence

ORD record
ord-dbf88b0c8bb5470a80f241f66360be31
Source dataset
uspto-grants-2002_04
Patent number
US06380249B1

Reaction notes

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