Benzenamine, 4-chloro-2-fluoro-5-(1-methylethoxy)- → 4-Chloro-2-fluoro-5-isopropoxyphenyl isocyanate

HRID 1379993Notes

Reaction equation

HRID 1379993 reaction equation
[Cl:1][C:2]1[C:8]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:7][C:5]([NH2:6])=[C:4]([F:13])[CH:3]=1.[C:14](Cl)(Cl)=[O:15].C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:8]([O:9][CH:10]([CH3:11])[CH3:12])=[CH:7][C:5]([N:6]=[C:14]=[O:15])=[C:4]([F:13])[CH:3]=1

Participants

4

Reactant 2

HCID 158649Benzenamine, 4-chloro-2-fluoro-5-(1-methylethoxy)-HCID 19083224Phosgen toluene

Product 1

HCID 132729244-Chloro-2-fluoro-5-isopropoxyphenyl isocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-chloro-2-fluoro-5-isopropoxyaniline (30 g) in toluene (100 ml) was added to a 1 mol/l phosgene/toluene solution (500 ml) at room temperature (ca. 20° C.), followed by heating under reflux for 2 hours. The mixture was concentrated under reduced pressure and the residue was distilled to give 26 g of 4-chloro-2-fluoro-5-isopropoxyphenyl isocyanate as pale yellow crystals. M.P., 36°-37° C. B.P., 90°-91° C./3 mmHg.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-bfd1141123a84de7882005ac3e8d61ba
Source dataset
uspto-grants-1986_04
Patent number
US04579688

Reaction notes

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