Hydrogen Bromide → HCID 23349415, compound

HRID 261135Notes

Reaction equation

HRID 261135 reaction equation
Br.[Br:2][CH2:3][C:4]1[C:10](Cl)=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6].[C:12](Cl)(Cl)=[O:13].C(Cl)([Cl:18])=O.C1C=CC=CC=1.Br>C1C=CC=CC=1>[Br:2][CH2:3][C:4]1[CH:10]=[C:9]([Cl:18])[CH:8]=[CH:7][C:5]=1[N:6]=[C:12]=[O:13]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 6371PhosgeneHCID 23349426HCID 23349426, compoundHCID 86736609HCID 86736609, compound

Product 1

HCID 23349415HCID 23349415, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.3 g of 2-bromomethyl-3-chloroaniline hydrobromide are added to 30 ml. of 12% phosgene in benzene. The mixture is heated to reflux in a 250 ml. flask fitted with a Dean-Stark trap and condenser. Small amounts of phosgene/benzene are carefully added until the hydrobromide is no longer detected (as indicated by following the reaction on thin layer chromatographic plates). The benzene solvent is removed from the reaction mixture by evaporation, then the 2-bromomethyl-4-chloroisocyanate product is recovered by vacuum distillation (at about 50° to 56° at about 0.05 to 0.03 mm Hg).

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux in a 250 ml
  3. customflask fitted with a Dean-Stark trap and condenser
  4. customthe reaction on thin layer chromatographic plates)
  5. customThe benzene solvent is removed from the reaction mixture by evaporation
  6. distillationthe 2-bromomethyl-4-chloroisocyanate product is recovered by vacuum distillation (at about 50° to 56° at about 0.05 to 0.03 mm Hg)

Sources & evidence

ORD record
ord-0df03840903d4951ad78c1533c62c9cf
Source dataset
uspto-grants-1979_08
Patent number
US04164407

Reaction notes

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