Sodium Iodide → HCID 67274136, compound

HRID 1695189Notes

Reaction equation

HRID 1695189 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([OH:12])=[C:7]([Cl:13])[CH:6]=1)C.[Na+].[I-].C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH:25]1[CH2:27][CH2:26]1>CC(C)=O>[CH3:1][O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][CH2:24][CH:25]2[CH2:27][CH2:26]2)=[C:7]([Cl:13])[CH:6]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 284603,5-Dichloro-4-hydroxybenzoic acid ethyl esterHCID 81503Bromomethylcyclopropane

Product 1

HCID 67274136HCID 67274136, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3,5-Dichloro-4-hydroxy-benzoic acid ethyl ester (1.0 g, 4.5 mmol, 1.0 eq) was dissolved in acetone (14 mL), NaI (0.5 eq) and K2CO3 (0.98 g, 9.0 mmol, 2.0 eq) were added ad the mixture was stirred at room temperature for 30 min. (Bromomethyl)cyclopropane (0.39 mL, 4.1 mmol, 0.9 eq) was added, and the mixture was refluxed for 2 days. The solvent was concentrated under reduced pressure, NaOH 10% was added, and it was extracted with DCM and dried. The title product (0.98 g, yield 79%) was recovered and used without further purification.

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed for 2 days
  3. concentrationThe solvent was concentrated under reduced pressure, NaOH 10%
  4. additionwas added
  5. extractionit was extracted with DCM
  6. customdried

Sources & evidence

ORD record
ord-3c50481b84ae47b898f20ad60943bebc
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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