Diphosgene → HCID 15766843, compound

HRID 2225938Notes

Reaction equation

HRID 2225938 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 100%

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 put in a 20-liter three-neck flask as equipped with a stirrer and a dropping funnel, and cooled in an ice-water bath. 5N sodium hydroxide aqueous solution (6 liters) was gradually added thereto with stirring vigorously. Next, trichloromethyl chloroformate (885 ml, 7.35 mol) was gradually dropwise added thereto over a period of about 6 hours. After addition, the reaction liquid was stirred overnight. After reaction, the organic layer was separated, and the aqueous layer was extracted with methylene chloride (1000 ml×2). The organic layers were combined, washed with 1N sodium hydroxide aqueous solution (4 liters) and water (5 liters) and then dried with anhydrous magnesium sulfate. The drying agent was taken out by filtration, and the solvent was removed from the organic layer by distillation under reduced pressure to obtain a white solid of bis(2-chloro-4-fluorophenyl)carbonate (4.9 kg, 5.4 mol). Yield: 100%. Spectral data and other data of the product are those as shown in Example 2.

Workup

  1. customas equipped with a stirrer and a dropping funnel
  2. temperaturecooled in an ice-water bath
  3. additionAfter addition
  4. customthe reaction liquid
  5. stirringwas stirred overnight
  6. customAfter reaction
  7. customthe organic layer was separated
  8. extractionthe aqueous layer was extracted with methylene chloride (1000 ml×2)
  9. washwashed with 1N sodium hydroxide aqueous solution (4 liters) and water (5 liters)
  10. dry with materialdried with anhydrous magnesium sulfate
  11. filtrationThe drying agent was taken out by filtration
  12. customthe solvent was removed from the organic layer by distillation under reduced pressure

Sources & evidence

ORD record
ord-4eb4785453a54761b88056837935b2b7
Source dataset
uspto-grants-1994_09
Patent number
US05344953

Reaction notes

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