Sodium Iodide → 4-Cyclopropylmethoxy-2-trifluoromethyl-benzoic acid methyl ester

HRID 1695187Notes

Reaction equation

HRID 1695187 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12].[Na+].[I-].C([O-])([O-])=O.[K+].[K+].Br[CH2:25][CH:26]1[CH2:28][CH2:27]1>CC(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:25][CH:26]2[CH2:28][CH2:27]2)=[CH:6][C:5]=1[C:11]([F:13])([F:12])[F:14]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 23109247Methyl 4-hydroxy-2-(trifluoromethyl)benzoate

Product 1

HCID 672744484-Cyclopropylmethoxy-2-trifluoromethyl-benzoic acid methyl esterYield 102.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-hydroxy-2-trifluoromethyl-benzoic acid methyl ester (1.1 g, 4.8 mmol, 1.0 eq) was dissolved in acetone (14 mL), NaI (0.5 eq) and K2CO3 (1.04 g, 2.0 eq) were added and the mixture was stirred at room temperature for 30 min. (Bromomethyl)cyclopropane (0.42 mL, 4.3 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 (1.21 g, yield 92%) 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-95dcd224e4dc4cc0b8990787b5e2f59e
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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