Propargyl bromide → Methyl 3,5-difluoro-4-(2-propynyloxy)benzoate

HRID 1675577Notes

Reaction equation

HRID 1675577 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[CH2:14](Br)[C:15]#[CH:16].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:13])[C:11]=1[O:12][CH2:16][C:15]#[CH:14])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 53847253Methyl 3,5-difluoro-4-hydroxybenzoate

Product 1

HCID 57445723Methyl 3,5-difluoro-4-(2-propynyloxy)benzoateYield 101.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 80 ml of acetonitrile were added 4.5 g of methyl 3,5-difluoro-4-hydroxybenzoate, 3.5 g of propargyl bromide and 9.4 g of cesium carbonate, and the resulting mixture was heated to reflux for 2 hours. Thereafter, the reaction mixture which had been allowed to cool to near room temperature was filtered through Celite (registered trade mark). The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography, and 5.5 g of methyl 3,5-difluoro-4-(2-propynyloxy)benzoate was obtained.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationwas filtered through Celite (registered trade mark)
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-16c52c34d7d342a49654f318c3f22d35
Source dataset
uspto-grants-2011_08
Patent number
US08003699B2

Reaction notes

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