Dimethylformamide → HCID 59301817, compound

HRID 1675572Notes

Reaction equation

HRID 1675572 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 resulting mixture was stirred at room temperature for 8 hours. Thereafter, ethyl acetate was added to the reaction mixture, and this was filtered through Celite (registered trade mark). Water and dilute hydrochloric acid were successively added to the filtrate, followed by extraction 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, and 10.8 g of 2-propynyl 4-(2-propynyloxy)-3-fluorobenzoate was obtained.

Workup

  1. filtrationthis was filtered through Celite (registered trade mark)
  2. additionWater and dilute hydrochloric acid were successively added to the filtrate
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-82c39be2fc7c443c84f107e8766e503e
Source dataset
uspto-grants-2011_08
Patent number
US08003699B2

Reaction notes

Loading…