Hydrogen Peroxide → 3-Fluoro-4-iodobenzamide

HRID 59406Notes

Reaction equation

HRID 59406 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[I:10])[C:5]#[N:6].C([O-])([O-])=[O:12].[K+].[K+].OO>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[I:10])[C:5]([NH2:6])=[O:12]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 247215213-Fluoro-4-iodobenzonitrile

Product 1

HCID 535838293-Fluoro-4-iodobenzamideYield 251,549.906%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-fluoro-4-iodobenzonitrile (2.7 g, 0.010 mmol) in DMSO (6.0 mL), K2CO3 (0.450 g, 0.003 mmol) and 30% H2O2 (2.4 mL) were added at 0-10° C. and the reaction mass was stirred at RT for 2 h. After completion of the reaction, the reaction mass was quenched in ice cold water. The obtained solid product was filtered off to afford 2.0 g of the desired title product. 1H NMR (400 MHz, DMSO d6): δ 7.48-7.51 (In, 2H), 7.66 (br s, 1H), 7.69-7.70 (m, 1H), 8.09 (brs, 1H).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mass was quenched in ice cold water
  3. filtrationThe obtained solid product was filtered off

Sources & evidence

ORD record
ord-a2621d3da56047a28120fdd334a8691c
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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