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

HRID 1675579Notes

Reaction equation

HRID 1675579 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. The mixture was stirred at room temperature for 30 minutes, and then at 80° C. for 1 hour. Thereafter, ethyl acetate was added to the reaction mixture which had been allowed to cool to near room temperature, and this was filtered through Celite (registered trade mark). To the filtrate were added successively water and dilute hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure, and 6.0 g of 2-propynyl 3,4,5-trifluorobenzoate was obtained.

Workup

  1. waitat 80° C. for 1 hour
  2. temperatureto cool to near room temperature
  3. filtrationthis was filtered through Celite (registered trade mark)
  4. additionTo the filtrate were added successively water and dilute hydrochloric acid
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c82e12adee0f42c8b9db5c706bbdb6ef
Source dataset
uspto-grants-2011_08
Patent number
US08003699B2

Reaction notes

Loading…