Hydrogen Peroxide → 3-Bromobenzamide

HRID 383259

Reaction equation

HRID 383259 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].OO.C([O-])([O-])=[O:13].[K+].[K+].O>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]([NH2:6])=[O:13]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 233813-Bromobenzonitrile

Product 1

HCID 898073-Bromobenzamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of m-bromobenzonitrile (2 g, 10 mol) in DMSO (6 mL) was added 30% H2O2 (5 g, 13 mmol) and K2CO3 at 0° C., and stirred at room temperature for 30 min. The mixture was poured into water and filtered, the solid was washed with water, dried to got the compound 0601-142 (1.8 g, 82%) as a white solid. LCMS: 200 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 7.41 (t, J=8.0 Hz, 1H), 7.50 (s, 1H), 7.70 (dd, J1,2=8.0, 0.8 Hz, 1H), 7.85 (d, J=8.0 Hz, 1H), 8.03 (t, J=1.6 Hz, 1H), 8.06 (s, 1H).

Workup

  1. filtrationfiltered
  2. washthe solid was washed with water
  3. customdried

Sources & evidence

ORD record
ord-3d3491c518b142a3b269daf0551cafbf
Source dataset
uspto-grants-2013_02
Patent number
US08367663B2

Linked notes

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