Potassium Carbonate → HCID 59428353, compound

HRID 503917Notes

Reaction equation

HRID 503917 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([Cl:15])[CH:9]=1.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1>CC(C)=O>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:22][C:21]2[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)=[C:10]([Cl:15])[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 198594-Bromo-2-chlorophenolHCID 1650214-Methoxybenzyl bromide

Product 1

HCID 59428353HCID 59428353, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (0.98 g, 7.086 mmol) was added to a solution of 4-bromo-2-chlorophenol (0.7 g, 3.374 mmol) and 4-methoxybenzylbromide (0.51 mL, 3.543 mmol) in acetone (20 mL) and the mixture was stirred at room temperature overnight. The solid phase was removed by filtration and the filtrate was evaporated to dryness under reduced pressure. The residue was partitioned between EtOAc and aqueous NaOH (2 M). The organic layer was washed with water and brine; dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 99/1) to give 0.937 g (85% yield) of 4-bromo-2-chloro-1-(4-methoxy-benzyloxy)-benzene as yellow solid.

Workup

  1. customThe solid phase was removed by filtration
  2. customthe filtrate was evaporated to dryness under reduced pressure
  3. customThe residue was partitioned between EtOAc and aqueous NaOH (2 M)
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified via flash chromatography (hexane/EtOAc, 99/1)

Sources & evidence

ORD record
ord-e1c417ea6ac74d1eb646d11af8f6d4b3
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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