Water → 4-Acetamido-3-iodobenzaldehyde

HRID 591679Notes

Reaction equation

HRID 591679 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[C:5]([I:13])[CH:4]=1.O>CS(C)=O>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[C:5]([I:13])[CH:4]=1)=[O:1]

Participants

4

Reactant 2

HCID 962WaterHCID 66745042N-(4-(Hydroxymethyl)-2-iodophenyl)acetamide

Product 1

HCID 229919464-Acetamido-3-iodobenzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of IBX (0.93 g, 3.3 mmol) in dimethylsulfoxide (3.5 mL) was added N-(4-hydroxymethyl-2-iodo-phenyl)-acetamide (0.87 g, 3.0 mmol) and the reaction mixture was stirred at room temperature for 1 hour. Water (50 mL) was added and the solid was separated by filtration, and washed with ethyl acetate (20 mL). The filtrate was collected and extracted with ethyl acetate (200 mL). The organic phase was washed with brine (100 mL) and dried over anhydrous Na2SO4. Removal of solvent gave N-(4-formyl-2-iodo-phenyl)-acetamide as a light brown solid. Yield: 0.82 g (95%).

Workup

  1. customthe solid was separated by filtration
  2. washwashed with ethyl acetate (20 mL)
  3. customThe filtrate was collected
  4. extractionextracted with ethyl acetate (200 mL)
  5. washThe organic phase was washed with brine (100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-932f32110be646afa950cb72c7fb2cf3
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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