Dimethylformamide → HCID 59301817, compound

HRID 602016Notes

Reaction equation

HRID 602016 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-d58e6d67d7ae4261ba27c768b4d86da1
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

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