Potassium Carbonate → HCID 21942664, compound

HRID 431870Notes

Reaction equation

HRID 431870 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([I:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[C:14](=O)([O-])[O-:15].[K+].[K+]>CO.O>[CH3:14][O:15][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([I:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 21942682HCID 21942682, compound

Product 1

HCID 21942664HCID 21942664, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of methyl 3-(bromomethyl)-5-iodobenzoate (400 mg, 1.1 mmol) and potassium carbonate (311 mg, 2.3 mmol) in methanol/tetrathydrofuran (5 mL/5 mL) was heated at 55° C. for 1 hour. After cooling, the reaction mixture was diluted with water and then extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. After drying in vacuo, 325 mg (94%) of methyl 3-(methoxymethyl)-5-iodobenzoate was isolated as a white solid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customAfter drying in vacuo

Sources & evidence

ORD record
ord-882256d715da40458c197558f2e247b3
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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