Dimethylformamide → 2-Propynyl 3,4,5-trifluorobenzoate

HRID 2236377Notes

Reaction equation

HRID 2236377 reaction equation
CN(C=O)C.[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([F:17])[C:15]=1[F:16])[C:10]([OH:12])=[O:11].[CH2:18](Br)[C:19]#[CH:20].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([F:17])[C:15]=1[F:16])[C:10]([O:12][CH2:20][C:19]#[CH:18])=[O:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 8531543,4,5-Trifluorobenzoic acid

Product 1

HCID 593017632-Propynyl 3,4,5-trifluorobenzoateYield 98.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 50 ml of DMF were added 5.0 g of 3,4,5-trifluorobenzoic acid, 4.0 g of propargyl bromide and 4.7 g of potassium carbonate, and the mixture obtained was stirred at room temperature for 30 minutes and then heated with stirring at 80° C. for 1 hour. Then, ethyl acetate was added to the reaction mixture and the mixture was filtered through Celite. Water and dilute hydrochloric acid were added to the filtrate in order and it was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to obtain 6.0 g of 2-propynyl 3,4,5-trifluorobenzoate represented by the formula:

Workup

  1. customthe mixture obtained
  2. temperatureheated
  3. stirringwith stirring at 80° C. for 1 hour
  4. filtrationthe mixture was filtered through Celite
  5. additionWater and dilute hydrochloric acid were added to the filtrate in order and it
  6. extractionwas extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-242fa91751574bceab4fc40f7aff901d
Source dataset
uspto-grants-2010_05
Patent number
US07714168B2

Reaction notes

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