Acetonitrile → 3,5-Difluoro-4-(2-propynyloxy)benzaldehyde

HRID 602023Notes

Reaction equation

HRID 602023 reaction equation
C(#N)C.[CH2:4]([OH:7])[C:5]#[CH:6].[F:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([F:18])[C:16]=1F)[CH:12]=[O:13].C(=O)([O-])[O-].[K+].[K+]>O>[F:18][C:15]1[CH:14]=[C:11]([CH:10]=[C:9]([F:8])[C:16]=1[O:7][CH2:4][C:5]#[CH:6])[CH:12]=[O:13]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7859Propargyl alcoholHCID 11430Potassium CarbonateHCID 27769543,4,5-Trifluorobenzaldehyde

Product 1

HCID 574456673,5-Difluoro-4-(2-propynyloxy)benzaldehydeYield 102%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of acetonitrile were added 12 g of propargyl alcohol, 16 g of 3,4,5-trifluorobenzaldehyde and 15 g of potassium carbonate, and the mixture obtained was stirred at room temperature for 1 day. Then, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid and brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 20 g of 3,5-difluoro-4-(2-propynyloxy)benzaldehyde represented by the formula:

Workup

  1. customthe mixture obtained
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with dilute hydrochloric acid and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11a02a62a95a423a950f9d749a3ad604
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

Loading…