Potassium Carbonate → HCID 57517515, compound

HRID 2368154Notes

Reaction equation

HRID 2368154 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH:9]1[CH2:11][CH2:10]1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21]>CN(C=O)C>[CH:11]1([CH2:10][O:19][C:16]2[CH:17]=[CH:18][C:13]([CH3:12])=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=2)[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 162713-Nitro-p-cresolHCID 81503Bromomethylcyclopropane

Product 1

HCID 57517515HCID 57517515, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (48.7 g) and (bromomethyl)cyclopropane (34.2 mL) were added to a solution of 4-methyl-3-nitrophenol (49.1 g) in DMF (320 mL) at room temperature, and the reaction mixture was stirred at 60° C. overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in diethyl ether, and the solution was washed 3 times with water. The aqueous layer was extracted again with diethyl ether, and the combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (66.4 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in diethyl ether
  3. washthe solution was washed 3 times with water
  4. extractionThe aqueous layer was extracted again with diethyl ether
  5. washthe combined organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-992fc5e8c3d14aa99d5fe92468402731
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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