Sodium Iodide → HCID 67015924, compound

HRID 1695185Notes

Reaction equation

HRID 1695185 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([Cl:11])[CH:5]=1.[Na+].[I-].C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH:23]1[CH2:25][CH2:24]1>CC(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:22][CH:23]2[CH2:25][CH2:24]2)=[C:6]([Cl:11])[CH:5]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 77580Methyl 3-chloro-4-hydroxybenzoateHCID 81503Bromomethylcyclopropane

Product 1

HCID 67015924HCID 67015924, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Chloro-4-hydroxy-benzoic acid methyl ester (1.1 g, 6.0 mmol, 1.0 eq) was dissolved in acetone (14 mL), NaI (0.45 g, 3.0 mmol, 0.5 eq) and K2CO3 (1.66 g, 12.0 mmol, 2.0 eq) were added ad the mixture was stirred at room temperature for 20 min. (Bromomethyl)cyclopropane (0.53 mL, 5.4 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 the crude was extracted with DCM and dried. The title product (0.88 g, yield 32%) 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. extractionthe crude was extracted with DCM
  6. customdried

Sources & evidence

ORD record
ord-86ac654af4d643bba76a5e682b22d56b
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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