Dimethylformamide → HCID 59301817, compound

HRID 2236368Notes

Reaction equation

HRID 2236368 reaction equation
CN([CH:4]=[O:5])C.[OH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][C:8]=1[F:16].[CH2:17](Br)[C:18]#[CH:19].C(=O)([O-])[O-].[K+].[K+].[C:27](OCC)(=O)[CH3:28]>>[CH2:17]([O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:5][CH2:4][C:27]#[CH:28])=[O:13])=[CH:9][C:8]=1[F:16])[C:18]#[CH:19]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1604563-Fluoro-4-hydroxybenzoic acid

Product 1

HCID 59301817HCID 59301817, compound

Procedure

To 50 ml of DMF were added 5.5 g of 4-hydroxy-3-fluorobenzoic acid, 9.4 g of propargyl bromide and 11 g of potassium carbonate, and the mixture was stirred at room temperature for 8 hours. Then, ethyl acetate was added to the reaction mixture and then, 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. The residue was subjected to silica gel column chromatography to obtain 10.8 g of 2-propynyl 4-(2-propynyloxy)-3-fluorobenzoate represented by the formula:

Workup

  1. filtrationthe mixture was filtered through Celite
  2. additionWater and dilute hydrochloric acid were added to the filtrate in order and it
  3. extractionwas extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96b0a22038834de5bfbd4c6e146c6863
Source dataset
uspto-grants-2010_05
Patent number
US07714168B2

Reaction notes

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