Potassium Carbonate → HCID 69288916, compound

HRID 2184358Notes

Reaction equation

HRID 2184358 reaction equation
[CH:1]1[C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=[C:3]([OH:12])[CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Br>CC(CC)=O.O>[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][O:10][C:9](=[O:11])[CH:8]=[CH:7][C:6]1[CH:5]=[CH:4][C:3]([O:12][CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[C:20]([F:19])[CH:21]=2)=[CH:2][CH:1]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 637542P-Coumaric Acid

Product 1

HCID 69288916HCID 69288916, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 5.0 g (30.5 mmol) p-cumaric acid, 8.4 g (61 mmol) potassium carbonate and 11.5 g (61 mmol) 3-fluorobenzylbromide in 500 ml ethyl methyl ketone is hold over night at 80° C. The reaction mixture is cooled, diluted with water and extracted with ethyl acetate. Chromatography (silica gel, n-hexane/ethyl acetate 4:1) gives 6.48 g (56%) of a colorless solid. MS: m/e=380.2 (M+).

Workup

  1. customat 80° C
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-ce616dbaf953421dab073bc69146c7dc
Source dataset
uspto-grants-2005_05
Patent number
US06900354B2

Reaction notes

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