HCID 68455108, compound → HCID 77230176, compound

HRID 2357549Notes

Reaction equation

HRID 2357549 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([F:10])[C:3]=1[I:11]>C(Cl)Cl.[O-2].[Mn+2]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[C:4]([F:10])[C:3]=1[I:11]

Participants

4

Reactant 1

HCID 68455108HCID 68455108, compound

Product 1

HCID 77230176HCID 77230176, compound

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-chloro-2-fluoro-3-iodophenyl)methanol (4.00 g, 14.0 mmol) in DCM (50 mL) was added manganese oxide (18.2 g, 209 mmol). The reaction mixture was refluxed for 10 h, then filtered through Celite® pad. The filtrate was concentrated under reduced pressure. Flash chromatography on silica gel (dichloromethane:hexane=20:80) gave 4-chloro-2-fluoro-3-iodobenzaldehyde as a white solid. MS (ESI, pos.ion) n/z: 286.2 (M+1)

Workup

  1. temperatureThe reaction mixture was refluxed for 10 h
  2. filtrationfiltered through Celite® pad
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d13d6a551c3d4b43b214d59d9e50f2b4
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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