1,4-Dioxane → 1-Bromo-5-chloro-3-fluoro-2-isocyanatobenzene

HRID 447758Notes

Reaction equation

HRID 447758 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([F:10])[C:3]=1[NH2:4].Cl[C:12]([O:15]C(=O)OC(Cl)(Cl)Cl)(Cl)Cl.O1CCOCC1>CO>[Br:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([F:10])[C:3]=1[N:4]=[C:12]=[O:15]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 94429TriphosgeneHCID 27362222-Bromo-4-chloro-6-fluoroaniline

Product 1

HCID 866189411-Bromo-5-chloro-3-fluoro-2-isocyanatobenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromo-4-chloro-6-fluoroaniline (5 mmol, 1.125 g), bis(trichloromethyl)carbonate (1.7 mmol, 0.50 g) and 1,4-dioxane (10 ml) were mixed together and the mixture was heated to 100° C. for 15 minutes; the mixture was then cooled to room temperature and it was filtered. The filtrate was concentrated to afford a mixture of products (2.2 g) containing the title compound, M++MeO=283 (LC-MS run in methanol).

Workup

  1. temperaturethe mixture was then cooled to room temperature
  2. filtrationit was filtered
  3. concentrationThe filtrate was concentrated
  4. customto afford

Sources & evidence

ORD record
ord-88c1552265f04242a7076c8c56a419cf
Source dataset
uspto-grants-2013_07
Patent number
US08481566B2

Reaction notes

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