1,3-Dibromopropane → 1,3-Bis(4-fluoro-2-iodophenoxy)propane

HRID 572953Notes

Reaction equation

HRID 572953 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1.Br[CH2:11][CH2:12][CH2:13]Br.[C:15](=[O:18])([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][CH2:12][CH2:13][O:18][C:15]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[I:9])=[C:4]([I:9])[CH:3]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 101714174-Fluoro-2-iodophenol

Product 1

HCID 667805951,3-Bis(4-fluoro-2-iodophenoxy)propane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 15.00 g (63.03 mmol) of 4-fluoro-2-iodophenol (P7), Preparation 7 and 6.40 g (31.68 mmol) of 1,3-dibromopropane in 200 mL of acetone add 26.00 g (188.4 mmol) of potassium carbonate. Reflux the resulting reaction mixture for 24 hours. Cool the reaction mixture to room temperature, filter it, and concentrate the filtrate by rotary evaporation. Crystallize the resulting solid from acetonitrile to yield 12.00 g (74%) of (P8) as a white crystalline solid.

Workup

  1. temperatureReflux
  2. customthe resulting reaction mixture for 24 hours
  3. filtrationfilter it
  4. concentrationconcentrate the filtrate
  5. customby rotary evaporation
  6. customCrystallize the resulting solid from acetonitrile
  7. customto yield 12.00 g (74%) of (P8) as a white crystalline solid

Sources & evidence

ORD record
ord-d97b5df56a5a4d84ba81625083555a2a
Source dataset
uspto-grants-2015_05
Patent number
US09029487B2

Reaction notes

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