Pyridine → HCID 18424482, compound

HRID 1282472Notes

Reaction equation

HRID 1282472 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:9][CH3:10])=[CH:4][CH:3]=1.[Br:18]Br.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.ClCCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)=[C:9]([Br:18])[CH3:10])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 24408BromineHCID 516892Sodium BicarbonateHCID 184244971,1'-(Prop-1-ene-1,1-diyl)bis(4-fluorobenzene)

Product 1

HCID 18424482HCID 18424482, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
-20 °C

Procedure

Into a reactor were introduced 2.00 g (8.69 mmol) of the 1,1-bis(4-fluorophenyl)propene and 25 mL of 1,2-dichloroethane under a nitrogen atmosphere. The contents were cooled to −20° C. A mixture of 1.39 g (8.69 mmol) of bromine and 12 mL of 1,2-dichloroethane was added dropwise thereto over 1 hour, and the resultant mixture was stirred at that temperature for 1 hour and then at room temperature for 16 hours. Subsequently, a solution prepared by mixing 0.703 mL (8.69 mmol) of pyridine with 20 mL of toluene was added dropwise thereto over 15 minutes, and this mixture was stirred at 100° C. for 2 hours and then cooled. Saturated aqueous sodium hydrogen carbonate solution was added to the resultant reaction mixture, which was then extracted with toluene. The resultant organic layer was washed with saturated aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was recrystallized from ethanol to obtain 1.21 g (45%) of the target compound as white crystals.

Workup

  1. additionwas added dropwise
  2. waitat room temperature for 16 hours
  3. customSubsequently, a solution prepared
  4. additionwas added dropwise
  5. waitover 15 minutes
  6. temperaturecooled
  7. customreaction mixture, which
  8. extractionwas then extracted with toluene
  9. washThe resultant organic layer was washed with saturated aqueous sodium chloride solution
  10. dry with materialdried with anhydrous magnesium sulfate
  11. customThereafter, the solvent was removed under reduced pressure
  12. customThe concentrate was recrystallized from ethanol

Sources & evidence

ORD record
ord-7479e3df3c184998a6537d36179ead22
Source dataset
uspto-grants-2002_09
Patent number
US06455720B1

Reaction notes

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