Potassium Carbonate → HCID 20429506, compound

HRID 615177Notes

Reaction equation

HRID 615177 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 204294997-Chlorodibenzofuran-3-ol

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, while stirring. The inorganic precipitate was filtered off under suction, the filtrate was evaporated down 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 2N sodium hydroxide solution and 100 ml of water in succession, dried over sodium sulfate and evaporated down under reduced pressure. The solid residue was left to stand with 30 ml of pentane at 0° C. for 30 minutes, after which it was filtered off under suction and washed with 30 ml of cold n-pentane. 77 g (50% of theory) of pure 1-bromo-3-(7-chlorodibenzofuran-3-yloxy)-propane of melting point 83°-85° C. were obtained.

Workup

  1. temperaturewas refluxed for 24 hours
  2. filtrationThe inorganic precipitate was filtered off under suction
  3. customthe filtrate was evaporated down 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 2N sodium hydroxide solution and 100 ml of water in succession
  6. dry with materialdried over sodium sulfate
  7. customevaporated down under reduced pressure
  8. waitThe solid residue was left
  9. filtrationafter which it was filtered off under suction
  10. washwashed with 30 ml of cold n-pentane

Sources & evidence

ORD record
ord-25e2d6c9e3584e8f922c4dbc9de14420
Source dataset
uspto-grants-1985_02
Patent number
US04497819

Reaction notes

Loading…