(3-Bromo-4-chlorophenyl)methanol → 3-Bromo-4-chlorobenzaldehyde

HRID 488842Notes

Reaction equation

HRID 488842 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][OH:6].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 50998689(3-Bromo-4-chlorophenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 140498093-Bromo-4-chlorobenzaldehydeYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-4-chlorobenzyl alcohol (2.73 g, 12.34 mmol) in dichloromethane (75 mL) was added, at room temperature, pyridinium chlorochromate (2.66 g, 12.34 mmol). The reaction mixture was stirred at room temperature for 1 hr then filtered over celite. The solvent was removed under reduced pressure and the residue chromatographed on silica gel (10% ethyl acetate in hexane) to afford 2.52 g of 3-bromo-4-chloro-benzaldehyde (93% yield). 1H NMR (300 MHz; CDCl3) 1H NMR (300 MHz; CDCl3) 7.65 (d, J=8.1 Hz, 1H); 7.78 (dd, J1=8.4 Hz, J2=2.1 Hz, 1H); 8.12 (d, J=2.1 Hz, 1H).

Workup

  1. filtrationthen filtered over celite
  2. customThe solvent was removed under reduced pressure
  3. customthe residue chromatographed on silica gel (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-cb523b4e75e34adab75b6ed62a0175ed
Source dataset
uspto-grants-2005_12
Patent number
US06974826B2

Reaction notes

Loading…