Potassium Carbonate → HCID 20429506, compound

HRID 354690

Reaction equation

HRID 354690 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]3[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:7]=3[O:8][C:4]=2[CH:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].Br[C:23]([Br:26])([CH3:25])C>C(C(C)=O)C>[Br:26][CH2:23][CH2:25][CH2:16][O:13][C:10]1[CH:11]=[CH:12][C:6]2[C:5]3[CH:14]=[CH:15][C:2]([Cl:1])=[CH:3][C:4]=3[O:8][C:7]=2[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 116582,2-DibromopropaneHCID 20429499HCID 20429499, compound

Product 1

HCID 20429506HCID 20429506, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 98.4 g (0.45 mole) of 7-chlorodibenzofuran-3-ol, 200 ml of methyl ethyl ketone, 93 g (0.67 mole) of potassium carbonate and 283 g (1.4 moles) of dibromopropane was refluxed for 24 hours. The inorganic precipitate was filtered off with suction and the filtrate was concentrated under reduced pressure. The residue was dissolved in 500 ml of methylene chloride and the solution was washed with 100 ml of water, 100 ml of 2 N sodium hydroxide solution and 100 ml of water in succession, dried over sodium sulfate and concentrated under reduced pressure. The solid residue was left to stand with 30 ml of pentane at 0° C. for 30 minutes, filtered off with suction and washed with 30 ml of cold n-pentane. 77 g of pure 1-bromo-3-(7-chlorodibenzofuran-3-oxy)-propane of melting point 83°-85° C. were obtained; yield: 50% of theory.

Workup

  1. temperaturewas refluxed for 24 hours
  2. filtrationThe inorganic precipitate was filtered off with suction
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in 500 ml of methylene chloride
  5. washthe solution was washed with 100 ml of water, 100 ml of 2 N sodium hydroxide solution and 100 ml of water in succession
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. waitThe solid residue was left
  9. filtrationfiltered off with suction
  10. washwashed with 30 ml of cold n-pentane

Sources & evidence

ORD record
ord-53aae8a75c18456fa8b709f87e828e9f
Source dataset
uspto-grants-1983_03
Patent number
US04376776

Linked notes

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