3-(4-Bromo-2-trifluoromethoxy-phenyl)-propan-1-ol → 3-(4-Bromo-2-trifluoromethoxy-phenyl)-propionaldehyde

HRID 1984906Notes

Reaction equation

HRID 1984906 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[C:4]([O:12][C:13]([F:16])([F:15])[F:14])[CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]=[O:11])=[C:4]([O:12][C:13]([F:14])([F:15])[F:16])[CH:3]=1

Participants

4

Reactant 2

HCID 689163273-(4-Bromo-2-trifluoromethoxy-phenyl)-propan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 866108663-(4-Bromo-2-trifluoromethoxy-phenyl)-propionaldehydeYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(4-bromo-2-trifluoromethoxy-phenyl)-propan-1-ol (1.03 g, 3.44 mmol) in CH2Cl2 (47 mL) was cooled at 4° C. and added celite (1.4 g) and pyridinium chlorochromate (1.11 g, 5.16 mmol). The reaction mixture was stirred at ambient temperature for 6 hr and filtered through a pad of celite, concentrated, and purified by flash chromatography (silica gel, 16% EtOAc in hexane) to give 3-(4-bromo-2-trifluoromethoxy-phenyl)-propionaldehyde (659 mg, 64%) as a colorless oil.

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationconcentrated
  3. custompurified by flash chromatography (silica gel, 16% EtOAc in hexane)

Sources & evidence

ORD record
ord-f92712ccc234470ebc0cde8fad85e4b0
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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