Potassium Carbonate → HCID 16433918, compound

HRID 2091040Notes

Reaction equation

HRID 2091040 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.Br[CH2:13][C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:8]([CH3:9])[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 959922-Acetyl-4-fluorophenol

Product 1

HCID 16433918HCID 16433918, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 1-(5-fluoro-2-hydroxyphenyl)ethanone (100 g), methyl bromoacetate (67.6 mL) and N,N-dimethylformamide (500 mL) was added potassium carbonate (135 g), and the mixture was stirred at 50° C. for 2 hr. The insoluble material was filtered off, 1,8-diazabicyclo[5.4.0]undec-7-ene (97.1 mL) was added, and the mixture was stirred at 120° C. for 30 min. 1N Hydrochloric acid was added to the reaction mixture at 0° C., and the resulting precipitate was collected by filtration to give the title object compound (77.9 g, 58%) as a white solid.

Workup

  1. filtrationThe insoluble material was filtered off
  2. addition1,8-diazabicyclo[5.4.0]undec-7-ene (97.1 mL) was added
  3. stirringthe mixture was stirred at 120° C. for 30 min
  4. addition1N Hydrochloric acid was added to the reaction mixture at 0° C.
  5. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-15f79f08237c474f81b1aa7dee6257f9
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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