N-bromobutanimide → 1-(4-Amino-3-bromo-phenyl)-cyclopropanecarbonitrile

HRID 1477470Notes

Reaction equation

HRID 1477470 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#[N:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:20])C(=O)C1>CC#N.CCOC(C)=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]#[N:12])[CH2:9][CH2:10]2)=[CH:6][C:7]=1[Br:20]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 138269361-(4-Aminophenyl)cyclopropanecarbonitrile

Product 1

HCID 688382611-(4-Amino-3-bromo-phenyl)-cyclopropanecarbonitrileYield 80.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-amino-phenyl)-cyclopropanecarbonitrile (96 mg, 0.60 mmol) in MeCN (3 mL) at 0° C. was added NBS (108 mg, 0.60 mmol) and the reaction was allowed to stir overnight. The reaction was diluted with EtOAc (25 mL) and was then washed with saturated aqueous NaHCO3 (1×25 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo to give 114 mg (80%) of 1-(4-amino-3-bromo-phenyl)-cyclopropanecarbonitrile. The crude product was used without further purification.

Workup

  1. washwas then washed with saturated aqueous NaHCO3 (1×25 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55e16492505e4c3c98431b9fc0e297aa
Source dataset
uspto-grants-2016_08
Patent number
US09403804B2

Reaction notes

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