Potassium Carbonate → HCID 19887239, compound

HRID 1722608Notes

Reaction equation

HRID 1722608 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].Br[CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH3:21])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70153241-Bromo-2-(2-ethoxyethoxy)ethaneHCID 7019368Methyl 3-fluoro-4-hydroxybenzoate

Product 1

HCID 19887239HCID 19887239, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 500-ml, round-bottom flask equipped with a magnetic stirrer, heating mantle and condenser were placed 5.7 g (33.5 mmol) methyl 3-fluoro-4-hydroxybenzoate, 8.5 g (43.2 mmol) 1-bromo-2-(2-ethoxyethoxy)-ethane, 23.2 g of powdered anhydrous potassium carbonate and 350 ml acetonitrile. After stirring the reaction mixture under reflux for four hours, TLC analysis showed that none of the phenolic starting material remained. Three hundred ml of the acetonitrile was then distilled off and 300 ml dichloromethane was added. The reaction mixture was filtered through Celite and the solids were washed thoroughly with dichloromethane. Evaporation of the filtrate yielded product in the form of a yellow oil. Purification by flash chromatography on silica gel with 4% diethyl ether in dichloromethane, followed by low temperature recrystallization from pentane, yielded 8.55 g of white crystals, 89%, m.p. 33-36.5° C. The structure was confirmed by infrared, nuclear magnetic resonance and mass spectral analyses. ##STR22##

Workup

  1. customInto a 500-ml, round-bottom flask equipped with a magnetic stirrer
  2. temperatureheating mantle and condenser
  3. temperatureunder reflux for four hours
  4. distillationThree hundred ml of the acetonitrile was then distilled off
  5. addition300 ml dichloromethane was added
  6. filtrationThe reaction mixture was filtered through Celite
  7. washthe solids were washed thoroughly with dichloromethane
  8. customEvaporation of the filtrate
  9. customyielded product in the form of a yellow oil
  10. customPurification by flash chromatography on silica gel with 4% diethyl ether in dichloromethane
  11. customfollowed by low temperature recrystallization from pentane

Sources & evidence

ORD record
ord-e4e7d2172098479ca86b1c37024259f7
Source dataset
uspto-grants-1989_08
Patent number
US04857227

Reaction notes

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