Phosgene → HCID 15766843, compound

HRID 275092Notes

Reaction equation

HRID 275092 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[OH-].[Na+].[C:12]([Cl:15])(Cl)=O.Cl[C:17]([O:19][C:20](Cl)(Cl)Cl)=[O:18]>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:17](=[O:18])[O:19][C:20]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:12]=1[Cl:15]

Participants

7

Reactant 4

HCID 6371Phosgene2×HCID 10426DiphosgeneHCID 14798Sodium HydroxideHCID 748142-Chloro-4-fluorophenol

Product 1

HCID 15766843HCID 15766843, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 297MethaneCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-4-fluorophenol (733 g, 5.0 mol) and methylene chloride (2.5 liters) were put in a 5-liter three-neck flask as equipped with a stirrer, and 4N sodium hydroxide aqueous solution (1350 ml) was added thereto and stirred with cooling. To the resulting solution was introduced phosgene as generated by decomposing trichloromethyl chloroformate (148 ml, 243 g, 1.23 mol) on an active charcoal (3.8 g) at a temperature of 40° to 50° C. After introduction of phosgene, the reaction solution was further stirred overnight at room temperature. After the reaction, the organic layer was separated, and the aqueous layer was extracted with methylene chloride (500 ml×2). The organic layers were combined, washed with 1N sodium hydroxide aqueous solution (1000 ml) and water, and thereafter dried with anhydrous magnesium sulfate. The drying agent was removed, and the solvent was removed by distillation under reduced pressure to obtain a white solid of bis (2-chloro-4-fluorophenyl)carbonate (801 g, 5.0 mol ). Yield: 100%.

Workup

  1. customas equipped with a stirrer
  2. temperaturewith cooling
  3. customat a temperature of 40° to 50° C
  4. customAfter the reaction
  5. customthe organic layer was separated
  6. extractionthe aqueous layer was extracted with methylene chloride (500 ml×2)
  7. washwashed with 1N sodium hydroxide aqueous solution (1000 ml) and water
  8. dry with materialdried with anhydrous magnesium sulfate
  9. customThe drying agent was removed
  10. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-8983b4a333f542c59df2397002bf9ce6
Source dataset
uspto-grants-1995_02
Patent number
US05391807

Reaction notes

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