Potassium Carbonate → HCID 13079914, compound

HRID 1589353Notes

Reaction equation

HRID 1589353 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([F:15])[CH:9]=1.[Cl-].[P:17]([O-])([S:22][CH2:23][CH2:24][CH3:25])([O:19][CH2:20][CH3:21])=[O:18]>C(#N)C>[P:17]([O:14][C:11]1[CH:12]=[CH:13][C:8]([Br:7])=[CH:9][C:10]=1[F:15])([S:22][CH2:23][CH2:24][CH3:25])([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenolHCID 131714521HCID 131714521, compound

Product 1

HCID 13079914HCID 13079914, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.5 g of potassium carbonate are added to 7.5 g of the resulting 4-bromo-2-fluorophenol in 100 ml of acetonitrile and the mixture is refluxed for one hour, with stirring. 7.5 g of O-ethyl S-n-propyl thiophosphate-chloride are then added dropwise at 50° C. and the mixture is stirred at this temperature for 3 hours and then at room temperature for 24 hours. The solvent is removed on a rotary evaporator, 400 ml of toluene and 100 ml of water are added, the phases are separated, the organic phase is washed with 2N sodium hydroxide solution and then with water and is dried with sodium sulfate, and the solvent and volatile impurities are stripped off under reduced pressure at 40° C./0.13 mbar. 7.5 g of O-ethyl S-n-propyl O-(4-bromo-2-fluorophenyl) thiophosphate are obtained as the residue; nD21 =1.5269.

Workup

  1. temperaturethe mixture is refluxed for one hour
  2. stirringthe mixture is stirred at this temperature for 3 hours
  3. customThe solvent is removed on a rotary evaporator, 400 ml of toluene and 100 ml of water
  4. additionare added
  5. customthe phases are separated
  6. washthe organic phase is washed with 2N sodium hydroxide solution
  7. dry with materialwith water and is dried with sodium sulfate
  8. customare stripped off under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-ed8ec9cedfe34614973d008ae11f620d
Source dataset
uspto-grants-1986_02
Patent number
US04569930

Reaction notes

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