Potassium Iodide → HCID 68859786, compound

HRID 493513Notes

Reaction equation

HRID 493513 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:22][O:21][C:19](=[O:20])[CH2:18][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 1380784-Hydroxy-4'-nitrobiphenyl

Product 1

HCID 68859786HCID 68859786, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4′-hydroxy-4-nitro-biphenyl (2.00 g, 7.51 mmol), prepared in the previous step, methyl bromoacetate (853 mL, 9.02 mmol) and potassium iodide (86 mg, 0.75 mmol) in 50 mL of acetone was stirred at room temperature until the mixture became cloudy. Potassium carbonate (2.26 g, 16.4 mmol) was added and the reaction refluxed overnight. The reaction was concentrated under reduced pressure and the residue partitioned between methylene chloride and water. The organic layer was separated, washed with water, dried (Na2SO4) and the solvent removed under reduced pressure to give (4′-nitro-biphenyl-4-yloxy)-acetic acid methyl ester.

Workup

  1. temperaturethe reaction refluxed overnight
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customthe residue partitioned between methylene chloride and water
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4e6a1ff5325c4ef68843b0b8109f99d4
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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