Triphosgene → 1-Bromo-3-isocyanato-2-methyl-benzene

HRID 628499Notes

Reaction equation

HRID 628499 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[CH3:9].Cl[C:11](Cl)([O:13]C(=O)OC(Cl)(Cl)Cl)Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]=[C:11]=[O:13])[C:3]=1[CH3:9]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 1235383-Bromo-o-toluidine

Product 1

HCID 655423311-Bromo-3-isocyanato-2-methyl-benzeneYield 106.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-bromo-2-methyl-3-aminobenzene 25.0 g, triphosgene 60.0 g and toluene 400 ml was stirred with heating under reflux for three hours. The reaction mixture after standing to cool was concentrated under reduced pressure to give 1-bromo-3-isocyanato-2-methylbenzene 30.3 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for three hours
  3. temperatureto cool
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-5f6203d8a4e94671af14d4942d38cdf1
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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