Sodium Iodide → Methyl 3-(2-(benzyloxy)-5-bromophenyl)-3-phenylpropanoate

HRID 227196

Reaction equation

HRID 227196 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH2:6][CH:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:19](=O)([O-])[O-:20].[K+].[K+].Cl[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[I-].[Na+]>CO.CC(C)=O>[CH2:26]([O:8][C:9]1[CH:10]=[CH:11][C:2]([Br:1])=[CH:3][C:4]=1[CH:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][C:7]([O:20][CH3:19])=[O:12])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 29249736-Bromo-3,4-dihydro-4-phenyl-2H-1-benzopyran-2-one

Product 1

HCID 21476697Methyl 3-(2-(benzyloxy)-5-bromophenyl)-3-phenylpropanoateYield 102.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

6-Bromo-4-phenyl-3,4-dihydro-coumarine (290 g, 0.96 mole) was dissolved in a mixture of methanol (1 L) and acetone (1 L). To the above solution were added potassium carbonate (160 g, 1.16 mole), α-chlorotoluene (140 g, 1.1 mole) and sodium iodide (30 g, 0.47 mole), and the mixture was stirred under reflux for 3 h. The solution was concentrated by distillation, and the residue treated with water and extracted with diethyl ether. The ethereal layer was washed with water, saturated sodium carbonate solution and water, successively. The organic layer was dried over sodium sulfate, filtered and then evaporated to give 420 g (≈100%) of the title compound as a light yellow oil.

Workup

  1. temperatureunder reflux for 3 h
  2. concentrationThe solution was concentrated by distillation
  3. additionthe residue treated with water
  4. extractionextracted with diethyl ether
  5. washThe ethereal layer was washed with water, saturated sodium carbonate solution and water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-7f6db4f2f8654539bef679b64303df3a
Source dataset
uspto-grants-2009_07
Patent number
USRE040851E1

Linked notes

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