Diphosgene → HCID 15766843, compound

HRID 742428Notes

Reaction equation

HRID 742428 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[OH-].[Na+].Cl[C:13]([O:15][C:16](Cl)(Cl)Cl)=[O:14]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][C:13](=[O:14])[O:15][C:16]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[Cl:1]

Participants

6

Reactant 3

HCID 10426DiphosgeneHCID 14798Sodium HydroxideHCID 748142-Chloro-4-fluorophenol

Product 1

HCID 15766843HCID 15766843, compoundYield 209.5%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-4-fluorophenol (4.4 Kg, 30 mol), triethylbenzylammonium chloride (17.1 g) and methylene chloride (7 liters) were placed in a 20L three-necked flask equipped with a stirrer and a dropping funnel and cooled in an ice bath. Then, a 5N aqueous sodium hydroxide solution (6 liters) was slowly added thereto, followed by stirring vigorously. Then, trichloromethyl chloroformate (885 ml, 7.35 mol) was added dropwise thereto slowly over about 6 hours at room temperature, and, after dropwise addition, the reaction solution was stirred overnight. After completion of the reaction, the organic layer was separated, and the aqueous layer was extracted with methylene chloride (1000 ml×2 portions). The organic layers were combined, washed with a 1N aqueous sodium hydroxide solution (4 liters) and water (5 liters), and dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the solvent was distilled off from the organic layer under reduced pressure to obtain bis(2-chloro-4-fluorophenyl)carbonate as a white solid (4.9 Kg, 15.4 mol, 100% yield).

Workup

  1. customequipped with a stirrer and a dropping funnel
  2. temperaturecooled in an ice bath
  3. additionafter dropwise addition
  4. stirringthe reaction solution was stirred overnight
  5. customAfter completion of the reaction
  6. customthe organic layer was separated
  7. extractionthe aqueous layer was extracted with methylene chloride (1000 ml×2 portions)
  8. washwashed with a 1N aqueous sodium hydroxide solution (4 liters) and water (5 liters)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customAfter removing the drying agent
  11. filtrationby filtration
  12. distillationthe solvent was distilled off from the organic layer under reduced pressure

Sources & evidence

ORD record
ord-2c8d0a350b0941908427b624bb0adf3d
Source dataset
uspto-grants-1996_09
Patent number
US05554581

Reaction notes

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