Potassium Chloride → HCID 12922713, compound

HRID 1702507Notes

Reaction equation

HRID 1702507 reaction equation
[C:1]1([O:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11](Br)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1([O-:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Na+].[Cl-].[K+].COCCOCCOC>[Cu].C1(C)C=CC=CC=1>[C:1]1([O:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([O:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 4873Potassium ChlorideHCID 8150DiglymeHCID 4445035Phenolate SodiumHCID 12922712HCID 12922712, compound

Product 1

HCID 12922713HCID 12922713, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 84.3 g (0.3 mol) of 3-bromo-4-fluorobenzyl phenyl ether, 34.8 g (0.3 mol) of sodium phenolate, 7 g (0.11 mol) of copper powder, 10 g of potassium chloride and 50 ml of bis-(2-methoxyethyl) ether (diglyme) was heated to 160° C. for 5 hours, while stirring. The reaction batch was then cooled to 80° C., 300 ml of toluene were added and the mixture was filtered. The filtrate was washed once with 100 ml of 10% strength sodium sulphate and was then extracted twice by shaking with 300 ml of water each time. The organic phase was dried over magnesium sulphate and the solvent was stripped off under a waterpump vacuum. The oily residue was distilled in vacuo. 70.7 g (80.2% of theory) of 4-fluoro-3-phenoxy-benzyl phenyl ether with the boiling point 195°-197° C./3 mbars were obtained as a very viscous oil.

Workup

  1. temperatureThe reaction batch was then cooled to 80° C.
  2. filtrationthe mixture was filtered
  3. washThe filtrate was washed once with 100 ml of 10% strength sodium sulphate
  4. extractionwas then extracted twice
  5. stirringby shaking with 300 ml of water each time
  6. dry with materialThe organic phase was dried over magnesium sulphate
  7. distillationThe oily residue was distilled in vacuo

Sources & evidence

ORD record
ord-8a49bb0bb1bd42fe9d601c8c22bb7c41
Source dataset
uspto-grants-1983_04
Patent number
US04381412

Reaction notes

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