Allyl bromide → HCID 67446969, compound

HRID 1019837Notes

Reaction equation

HRID 1019837 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:20][CH:21]=[CH2:22]>CC(C)=O>[CH2:22]([O:12][C:4]1[CH:3]=[C:2]([F:1])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH:21]=[CH2:20]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 2775386Methyl 4-fluorosalicylate

Product 1

HCID 67446969HCID 67446969, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 4-fluoro-2-hydroxybenzoate (0.27 mol), K2CO3 (0.41 mol), and KI (27 mmol) were charged in a 1-l reactor under N2. Acetone (500 ml) was added, followed by 3-bromo-propene (0.33 mol). The mixture was refluxed for 6 h under N2. The mixture was cooled to room temperature and filtered to remove the solid. The solvent was removed under vacuum, and the residue dissolved in water (200 ml) and CH2Cl2 (300 ml). The organic and aqueous layers were separated and the aqueous phase extracted with CH2Cl2. The organic layers were combined and dried with Na2SO4. The solvent was removed under vacuum to give Intermediate I-40 as a white solid.

Workup

  1. temperatureThe mixture was refluxed for 6 h under N2
  2. filtrationfiltered
  3. customto remove the solid
  4. customThe solvent was removed under vacuum
  5. dissolutionthe residue dissolved in water (200 ml)
  6. customThe organic and aqueous layers were separated
  7. extractionthe aqueous phase extracted with CH2Cl2
  8. dry with materialdried with Na2SO4
  9. customThe solvent was removed under vacuum
  10. customto give Intermediate I-40 as a white solid

Sources & evidence

ORD record
ord-0ed9962036924e6c8f5ca6349492ebe1
Source dataset
uspto-grants-2014_05
Patent number
US08716293B2

Reaction notes

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