Potassium Carbonate → HCID 86666271, compound

HRID 1026239Notes

Reaction equation

HRID 1026239 reaction equation
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.[Br:6][C:7]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:8]=1[CH2:14][C:15]([OH:17])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:6][C:7]1[CH:12]=[C:11]([O:13][CH2:2][CH:3]2[CH2:5][CH2:4]2)[CH:10]=[CH:9][C:8]=1[CH2:14][C:15]([O:17][CH2:2][CH:3]1[CH2:5][CH2:4]1)=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 24721648(2-Bromo-4-hydroxyphenyl)acetic acid

Product 1

HCID 86666271HCID 86666271, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (bromomethyl)cyclopropane (10.52 g), (2-bromo-4-hydroxyphenyl)acetic acid (6.0 g) and potassium carbonate (7.18 g) in DMF (200 mL) was stirred at 80° C. for 8 hr. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. The residue was diluted with diethyl ether and water, and the organic layer was separated. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (7.89 g).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionThe residue was diluted with diethyl ether and water
  3. customthe organic layer was separated
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-94c7ae5292e242dc90446a9558102a27
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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