Hydrochloric Acid → 4-Bromo-2-fluoro-1-(isocyanatomethyl)benzene

HRID 726842

Reaction equation

HRID 726842 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([F:10])[CH:3]=1.Cl.Cl.BrC1C=CC(CN)=C(F)C=1.[C:23](Cl)(Cl)=[O:24]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:7]=[C:23]=[O:24])=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6371PhosgeneHCID 3770848(4-Bromo-2-fluorophenyl)methanamineHCID 184681974-Bromo-2-fluorobenzylamine hydrochloride

Product 1

HCID 158174014-Bromo-2-fluoro-1-(isocyanatomethyl)benzeneYield 92.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-bromo-2-fluorobenzylamine (20.4 g, 0.10 mol) in toluene (300 ml) is saturated with gaseous hydrochloric acid at 25° C. The resulting suspension of the 4-bromo-2-fluorobenzylamine hydrochloride is heated at 100° C. Phosgene is passed in at this temperature. Stirring of the solution, which has eventually become clear, is continued at 100° C. for 1 hour, and the mixture is then refluxed to remove the gases phosgene and hydrogen chloride. The batch is worked up by distillation. 21.2 g of 4-bromo-2-fluorobenzyl isocyanate (boiling point 109° C. at 4 mbar) are obtained. Yield: 92.1% of theory.

Workup

  1. temperaturethe mixture is then refluxed
  2. customto remove the gases phosgene and hydrogen chloride
  3. distillationThe batch is worked up by distillation

Sources & evidence

ORD record
ord-f9950dc95a94410486aae253107a9552
Source dataset
uspto-grants-1998_01
Patent number
US05710319

Linked notes

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