3-Fluoro-5-iodobenzyl alcohol → 3-Fluoro-5-iodobenzaldehyde

HRID 595995Notes

Reaction equation

HRID 595995 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[C:6]([I:8])[CH:7]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([I:8])[CH:7]=1)[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 916589643-Fluoro-5-iodobenzyl alcoholHCID 178418287HCID 178418287, compound

Product 1

HCID 269863443-Fluoro-5-iodobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-fluoro-5-iodophenyl)methanol (9.79 g, 35.0 mmol) was dissolved in DCM (94 mL) and then silica gel (18.0 g) was added. To the mixture at room temperature was added PCC (18.3 g, 45.0 mmol) portion-wise and the mixture agitated at room temperature for 1 h and followed by TLC. After 1 h, TLC indicated complete conversion of the SM to a non-polar (presumably aldehyde). The reaction mixture was filtered over 1-inch plug of silica pad and eluted with 30% Ether in DCM (200 mL). The filtrate was concentrated in vacuo to afford the crude product, which was taken to the next step without further purification.

Workup

  1. additionsilica gel (18.0 g) was added
  2. waitAfter 1 h
  3. filtrationThe reaction mixture was filtered over 1-inch plug of silica pad
  4. washeluted with 30% Ether in DCM (200 mL)
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e57a40423d9b437496e0cad4429817b3
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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