HCID 67173090, compound → 2-Fluoro-3-iodo-4-methylbenzaldehyde

HRID 2357517Notes

Reaction equation

HRID 2357517 reaction equation
[F:1][C:2]1[C:7]([I:8])=[C:6]([CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][OH:11]>C(Cl)Cl.O=[Mn]=O>[F:1][C:2]1[C:7]([I:8])=[C:6]([CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]=[O:11]

Participants

4

Reactant 1

HCID 67173090HCID 67173090, compound

Product 1

HCID 587021552-Fluoro-3-iodo-4-methylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (2-fluoro-3-iodo-4-methylphenyl)methanol (1.69 g, 6.35 mmol) in DCM (50 mL) at ambient temperature was treated with MnO2 (5.57 g, 63.5 mmol) and the resulting mixture was stirred overnight. The mixture was filtered through a pad of Celite® eluting with DCM. The filtrate was concentrated and the residue was loaded on an ISCO column (40 g, eluted with 15-35% ethyl acetate in hexanes) to provide 2-fluoro-3-iodo-4-methylbenzaldehyde as an off white solid. MS (ESI, pos. ion) m/z: 264.9 (M+1).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. washeluting with DCM
  3. concentrationThe filtrate was concentrated
  4. washthe residue was loaded on an ISCO column (40 g, eluted with 15-35% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-252248dfe29446c4861448fbf29ce1f8
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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