Oxalyl chloride → 1,3-Dichloro-2-(2,2-dichloro-1,1-difluoroethoxy)-5-isocyanatobenzene

HRID 485220Notes

Reaction equation

HRID 485220 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[CH:5]=[C:6]([Cl:15])[C:7]=1[O:8][C:9]([F:14])([F:13])[CH:10]([Cl:12])[Cl:11].C(Cl)(=O)[C:18](Cl)=[O:19]>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:16]=[C:18]=[O:19])[CH:5]=[C:6]([Cl:15])[C:7]=1[O:8][C:9]([F:14])([F:13])[CH:10]([Cl:12])[Cl:11]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 13338272HCID 13338272, compound

Product 1

HCID 133382731,3-Dichloro-2-(2,2-dichloro-1,1-difluoroethoxy)-5-isocyanatobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3,5-Dichloro-4-(2,2-dichloro-1,1-difluoroethoxy)benzenamine (12 g, 0.04 mole) was added to a solution of 20 g oxalyl chloride in 100 ml CCl4 and heated under reflux with stirring for 0.5 hour. A solid precipitated. The carbon tetrachloride and excess oxalyl chloride were removed by evaporation in a rotary evaporator. The residue (16 g) was a slightly oily white solid, which was used in the next reaction without purification.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customA solid precipitated
  4. customThe carbon tetrachloride and excess oxalyl chloride were removed by evaporation in a rotary evaporator
  5. customwas used in the next reaction without purification

Sources & evidence

ORD record
ord-ab55cccac57c45b39ed45887c6d9f088
Source dataset
uspto-grants-1985_08
Patent number
US04536341

Reaction notes

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