Ethylene carbonate → Phenyl Fluoroformate

HRID 1166633Notes

Reaction equation

C1(=O)OCCO1.[F-:7].[K+].Cl[C:10]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11].ClC([O-])=O>>[F:7][C:10]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11]

Participants

Reactant 4

HCID 7303Ethylene carbonate

HCID 15891Phenyl chloroformate

HCID 522689Potassium Fluoride

HCID 21226386Carbonochloridate

Product 1

HCID 11815898Phenyl FluoroformateYield 93.5%

Procedure

The preparation was carried out as in Example 2 but using 250 g of ethylene carbonate, 89 g (1.53 mol) of potassium fluoride and 156.6 g (1.0 mol) of phenyl chloroformate. After addition of the chloroformate, stirring of the reaction mixture was continued at 45°-50° C. for 2 hours. Evaporation under vacuum was carried out as above. By distillation under reduced pressure, 131 g (93.5% yield) of phenyl fluoroformate with a boiling point of 62°-64° at 40 mm Hg were recovered.

Workup

customEvaporation under vacuum

Sources & evidence

ORD record: ord-eb37e1517b4743b8acccb02a295a296c
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613929B2

Reaction notes

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