Bromine → 4-(Bromoacetyl)benzonitrile

HRID 379659Notes

Reaction equation

HRID 379659 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1)#[N:2].[Br:12]Br.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.Br>[Br:12][CH2:10][C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)=[O:11]

Participants

6

Reactant 3

HCID 24408BromineHCID 740444'-CyanoacetophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 986544-(Bromoacetyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 6212ChloroformSolvent2×

Procedure

To a mixture of para-cyanoacetophenone (52 g, 0.36 mol) in chloroform (520 ml) and 48% HBr (5.2 ml), a solution of bromine (19.3 ml) in chloroform (52 ml) was added dropwise over a period of 20 min. The mixture was stirred for 3 h at room temperature and neutralized to pH7 with sat. NaHCO3. The organic layer was washed with sat. NaCl and dried over anhydrous Na2SO4 and concentrated. The residue was chromatographed on silica gel (AcOEt/n-hexane=1/3 as an eluent) and recrystallized to obtain 2-bromo-4′-cyanoacetophenone as a colourless plate (23.4 g, 29%).

Workup

  1. washThe organic layer was washed with sat. NaCl
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel (AcOEt/n-hexane=1/3 as an eluent) and
  5. customrecrystallized

Sources & evidence

ORD record
ord-02ff5805384043bf8c9dbc67dccdc6b2
Source dataset
uspto-grants-2001_10
Patent number
US06300353B1

Reaction notes

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