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

HRID 602021Notes

Reaction equation

HRID 602021 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 mixture obtained was heated under reflux for 2 hours. The reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 5.5 g of methyl 3,5-difluoro-4-(2-propynyloxy)benzoate represented by the formula:

Workup

  1. customthe mixture obtained
  2. temperaturewas heated
  3. temperatureunder reflux for 2 hours
  4. filtrationThe reaction mixture was filtered through Celite
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-de203bc6b82c48a29ea1e70662f719c8
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

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