Cesium carbonate → HCID 68843931, compound

HRID 1784846Notes

Reaction equation

HRID 1784846 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[Br:11][C:12]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:13]=1[OH:19].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Br:11][C:12]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:13]=1[O:19][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 120052,4-DibromophenolHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 68843931HCID 68843931, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Methoxybenzylchloride (0.6 mL, 4.4 mmol) was added to a mixture of 2,4-dibromo-phenol (1 g, 4 mmol) and potassium carbonate (0.61 g, 4.4 mmol) in DMF (20 mL) at room temperature. The resulting mixture was stirred at room temperature for 1 hr. After adding cesium carbonate (1.3 g, 4 mmol), the resulting mixture was stirred at 90° C. for 2 hrs. The mixture was then cooled to room temperature, diluted with water, and extracted with EtOAc twice. The combined EtOAc extracts were washed with a mixture of water and brine several times, then concentrated to afford 1.45 g (98% yield) of 2,4-dibromo-1-(4-methoxy-benzyloxy)-benzene as a light yellow oil, which was used directly in the next reaction.

Workup

  1. stirringthe resulting mixture was stirred at 90° C. for 2 hrs
  2. temperatureThe mixture was then cooled to room temperature
  3. extractionextracted with EtOAc twice
  4. washThe combined EtOAc extracts were washed with a mixture of water and brine several times
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3547cc7b96ce462eb0b07ee1663ebfe7
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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