Hydrochloric Acid → HCID 11593499, compound

HRID 1669353Notes

Reaction equation

HRID 1669353 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]=[C:12]([F:14])[F:13])[CH:6]=1.[CH:15](N1CCCCC1)=[O:16].Cl>O1CCCC1>[F:13][C:12]([F:14])=[CH:11][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[CH:15]=[O:16]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 174291-PiperidinecarboxaldehydeHCID 5462224MagnesiumHCID 113564273-Bromo-beta,beta-difluorostyrene

Product 1

HCID 11593499HCID 11593499, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a mixture of 0.67 g of magnesium and 10 ml of tetrahydrofuran was added a catalytic amount of iodine, and added dropwise a solution of 6.0 g of 1-bromo-3-(2,2-difluoroethenyl)benzene in 20 ml of tetrahydrofuran at 55° C. After stirred at room temperature for 15 minutes, a solution of 3.98 g of 1-formylpiperidine in 5 ml of tetrahydrofuran was added dropwise. This was heated under reflux for 15 minutes, and ice water and 10% hydrochloric acid were added, followed by extraction with t-butyl methyl ether. The organic layer was washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated. The resulting residue was subjected to silica gel column chromatography to obtained 1.13 g of oily 3-(2,2-difluoroethenyl)benzaldehyde [Compound No. (1)].

Workup

  1. temperatureThis was heated
  2. temperatureunder reflux for 15 minutes
  3. extractionfollowed by extraction with t-butyl methyl ether
  4. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5ac1575064104f53afa1e1d6d162a245
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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