Water → 2-Amino-5-bromobenzonitrile

HRID 1844700Notes

Reaction equation

HRID 1844700 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C1C(=O)N([Br:17])C(=O)C1.O>CN(C=O)C>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Br:17])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 729132-Aminobenzonitrile

Product 1

HCID 4297402-Amino-5-bromobenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-aminobenzonitrile (14.9 g, 100 mmol) was added a solution of NBS (17.8 g, 100 mmol) in DMF at rt. The mixture was stirred overnight at rt, then water (30 mL) was added and the mixture was extracted with Et2O (3×250 mL). The organic layer was washed with brine, dried over Na2SO4, concentrated and purified by CC to give compound P36a (19 g, 83%).

Workup

  1. extractionthe mixture was extracted with Et2O (3×250 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by CC
  6. customto give compound P36a (19 g, 83%)

Sources & evidence

ORD record
ord-0fd4ded0ad144a7ba4eef0f5acf2889f
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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