2-Iodoxybenzoic acid → 2-(3-Fluoro-4-methoxy-phenyl)-cyclopropanecarbaldehyde

HRID 62898

Reaction equation

HRID 62898 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:12][CH:11]2[CH2:13][OH:14])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].I(C1C=CC=CC=1C(O)=O)(=O)=O>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:12][CH:11]2[CH:13]=[O:14])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 22347600[2-(3-Fluoro-4-methoxy-phenyl)-cyclopropyl]-methanol

Product 1

HCID 207922502-(3-Fluoro-4-methoxy-phenyl)-cyclopropanecarbaldehydeYield 89.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

After [2-(3-fluoro-4-methoxy-phenyl)-cyclopropyl]-methanol (0.30 g, 1.52 mmol) obtained in Step A was dissolved in DMSO (5 mL), 2-iodoxybenzoic acid (1.248 g, 4.58 mmol) was added thereto at 0° C., and the mixture was stirred at room temperature for 3 hours. After the termination of the reaction, the reactant was concentrated under reduced pressure, added with water, and then extracted with EtOAc. The organic layer was separated, dried with MgSO4, concentrated under reduced pressure, and then purified by column chromatography (eluent, EtOAc/Hex=1/3) to obtain the title compound (0.265 g, 89%).

Workup

  1. customAfter the termination of the reaction
  2. concentrationthe reactant was concentrated under reduced pressure
  3. additionadded with water
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated under reduced pressure
  8. custompurified by column chromatography (eluent, EtOAc/Hex=1/3)

Sources & evidence

ORD record
ord-11927d140f08417fa37a449300c73eae
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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