1,3-Dibromopropane → 1,3-Bis(2,4-difluoro-6-iodophenoxy)propane

HRID 1468470Notes

Reaction equation

HRID 1468470 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([I:9])[C:3]=1[OH:10].Br[CH2:12][CH2:13][CH2:14]Br.[C:16](=[O:19])([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([I:9])[C:3]=1[O:10][CH2:12][CH2:13][CH2:14][O:19][C:16]1[C:4]([I:9])=[CH:3][C:2]([F:1])=[CH:7][C:6]=1[F:8]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 222216242,4-Difluoro-6-iodophenol

Product 1

HCID 585165561,3-Bis(2,4-difluoro-6-iodophenoxy)propane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 7.68 g (30 mmol) of 2,4-difluoro-6-iodophenol (P7), Preparation 7 and 3.03 g (15 mmol) of 1,3-dibromopropane in 125 mL of acetone add 12.42 g (90 mmol) of potassium carbonate. Reflux the resulting reaction mixture for 48 hours. Cool the reaction mixture to room temperature, filter it, and extract the resulting filtrate thoroughly with methylene chloride. Combine methylene chloride extracts and concentrate them by rotary evaporation. Crystallize the resulting solid from hexanes to yield 3.4 g (41.1%) of (P8) as a white solid.

Workup

  1. temperatureReflux
  2. customthe resulting reaction mixture for 48 hours
  3. filtrationfilter it
  4. extractionextract the resulting filtrate thoroughly with methylene chloride
  5. concentrationconcentrate them
  6. customby rotary evaporation
  7. customCrystallize the resulting solid from hexanes
  8. customto yield 3.4 g (41.1%) of (P8) as a white solid

Sources & evidence

ORD record
ord-6902d52c34c04724a6c1cfadea210f36
Source dataset
uspto-grants-2015_04
Patent number
US09000108B2

Reaction notes

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