4-Bromo-3,5-dichloroaniline → 4-Amino-2,6-dichlorobenzonitrile

HRID 872768Notes

Reaction equation

HRID 872768 reaction equation
Br[C:2]1[C:8]([Cl:9])=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:10].[Cu][C:12]#[N:13]>CN(C=O)C>[NH2:6][C:5]1[CH:7]=[C:8]([Cl:9])[C:2]([C:12]#[N:13])=[C:3]([Cl:10])[CH:4]=1

Participants

4

Reactant 2

HCID 137497104-Bromo-3,5-dichloroanilineHCID 178418546HCID 178418546, compound

Product 1

HCID 596359894-Amino-2,6-dichlorobenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from the reaction of 4-bromo-3,5-dichloroaniline (6.88 g, 28.6 mmol) and Copper(I)cyanide (2.56 g, 28.6 mmol) in DMF (48 mL) under microwave irradiation at 190° C. for 1 h. After the completion of the reaction, the mixture was cooled to RT and quenched with 200 mL of 12% ammonia solution. The resultant mixture was stirred for 30 min at RT and the precipitate was filtered, washed with water and dried under vacuum. Yield 3.725 g. 1H NMR (400 MHz; d6-DMSO): δ 6.70 (s, 1H), 6.79 (s, 1H).

Workup

  1. customAfter the completion of the reaction
  2. customquenched with 200 mL of 12% ammonia solution
  3. filtrationthe precipitate was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-6485f9b0577847858166a497607fe179
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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