Water → 2-Bromo-5-isocyanato-1,3-dimethylbenzene

HRID 1754970Notes

Reaction equation

HRID 1754970 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[Br:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([NH2:21])=[CH:16][C:15]=1[CH3:22].O>O1CCOCC1>[Br:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([N:21]=[C:5]=[O:11])=[CH:16][C:15]=1[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 94429TriphosgeneHCID 123831174-Bromo-3,5-dimethylaniline

Product 1

HCID 866727652-Bromo-5-isocyanato-1,3-dimethylbenzeneYield 117.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Triphosgene (2.23 g, 7.52 mmol) was added to a solution of 4-bromo-3,5-dimethyl-phenylamine (4.3 g, 21.49 mmol) in dioxane (71 ml). After stirring at 100° C. for 15 hours, water was added to the reaction solution. After extraction with ethyl acetate, the organic phase was sequentially washed with water and saturated brine and concentrated under reduced pressure to give 2-bromo-5-isocyanato-1,3-dimethylbenzene (2.0 g, 41%).

Workup

  1. extractionAfter extraction with ethyl acetate
  2. washthe organic phase was sequentially washed with water and saturated brine
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fb602089dde1444fa16869f3eea4d148
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

Loading…