1,3-Dibromopropane → 4,4'-Trimethylenedioxydibenzonitrile

HRID 325058Notes

Reaction equation

HRID 325058 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[C:10](=[O:13])([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][CH2:19]Br>CN(C=O)C>[CH2:17]([O:13][C:10]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[CH2:18][CH2:19][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 130194-Cyanophenol

Product 1

HCID 819914,4'-TrimethylenedioxydibenzonitrileYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-cyanophenol (20.0 g; 0.16 mol) in DMF (350 mL) was added powdered potassium carbonate (34.8g; 0.25 mol) under an atmosphere of argon. This mixture was stirred at room temperature for 15 minutes. To the reaction mixture was added 1,3-dibromopropane (8.52 mL; 0.08 mol) via syringe, and the mixture stirred at room temperature for 16 hours. The solvent was removed by high vacuum distillation and the remaining white solid was taken up in 200 mL of EtOAc. HCl (1N in water) was then added and a white precipitate formed. This precipitate was collected by filtration, washed several times with diethyl ether, and then dried under vacuum. A total of 20.2 g of a white solid were obtained (90% yield).

Workup

  1. stirringthe mixture stirred at room temperature for 16 hours
  2. customThe solvent was removed by high vacuum distillation
  3. additionHCl (1N in water) was then added
  4. customa white precipitate formed
  5. filtrationThis precipitate was collected by filtration
  6. washwashed several times with diethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-b0c50ea423ff4314be684ee43e66f1de
Source dataset
uspto-grants-2001_04
Patent number
US06221914B1

Reaction notes

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