Hydrochloric Acid → 3-Bromophenyl isocyanate

HRID 49550

Reaction equation

HRID 49550 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl.[C:10](OCC)(=[O:12])C>C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([N:5]=[C:10]=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 115623-Bromoaniline

Product 1

HCID 1410013-Bromophenyl isocyanateYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-Bromoaniline (2.63 g, 15.3 mmol) was dissolved in ethyl acetate (100 ml) and 1N dry hydrogen chloride in diethyl ether (15.3 ml) was added and the solvents were removed in vacuo. The residue was stripped twice with toluene and the residue was suspended in toluene (30 ml). Diphosgene (6.1 ml) was added and the mixture was refluxed for 1.5 hour. After cooling, the solution was concentrated in vacuo to afford 2.63 g (87%) 3-bromophenyliso-cyanate.

Workup

  1. customthe solvents were removed in vacuo
  2. additionDiphosgene (6.1 ml) was added
  3. temperaturethe mixture was refluxed for 1.5 hour
  4. temperatureAfter cooling
  5. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-6e7461da49db41cc9a495add858cf3e5
Source dataset
uspto-grants-2004_03
Patent number
US06706744B2

Linked notes

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