Ethyl Acetate → HCID 14370871, compound

HRID 1199602Notes

Reaction equation

HRID 1199602 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([Br:9])[C:6]([O:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:3]=1[NH2:4].[C:15](OCC)(=[O:17])C>>[F:1][C:2]1[CH:8]=[C:7]([Br:9])[C:6]([O:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:3]=1[N:4]=[C:15]=[O:17]

Participants

3

Reactant 2

HCID 8857Ethyl Acetate2×HCID 14370869HCID 14370869, compound

Product 1

HCID 14370871HCID 14370871, compoundYield 94%

Conditions

Temperature
80 °C

Procedure

A solution of trichloromethyl chloroformate trichloromethyl (15 ml, 125 mmol) in ethyl acetate was charged into a 500 ml-three neck flask equipped with a dropping funnel and distillation apparatus and, a solution of 2-fluoro-4-bromo-5-methoxycarbonyloxyaniline (28.0 g,113 mmol) in ethyl acetate (100 ml) was added dropwise over 20 minutes. After dropping, the mixture was heated at 80° C. and ethyl acetate was removed by distillation. After cooling, carbon tetrachloride (150 ml) was added and the undissolved substances were removed by filtration. The solvent was then removed from the filtrate by distillation under reduced pressure, whereby a brown solid of 2-fluoro-4-bromo-5-methoxycarbonyloxyphenyl isocyanate (29.1 g, yield 94%) was obtained.

Workup

  1. customequipped with a dropping funnel
  2. distillationdistillation apparatus
  3. customethyl acetate was removed by distillation
  4. temperatureAfter cooling
  5. additioncarbon tetrachloride (150 ml) was added
  6. customthe undissolved substances were removed by filtration

Sources & evidence

ORD record
ord-6b8ccc9400fa4e49b92fb48100c5052e
Source dataset
uspto-grants-1990_02
Patent number
US04902337

Reaction notes

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