Diethyl Ether → 4-Bromo-2-chlorobenzaldehyde

HRID 2247754Notes

Reaction equation

HRID 2247754 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([Cl:10])[CH:3]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.CCOCC>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[C:4]([Cl:10])[CH:3]=1

Participants

5

Procedure

To a solution of (4-bromo-2-chlorophenyl)methanol (2.8 g, 12.8 mmol) that was obtained in Example 24 (24e) in dichloromethane (50 ml) was added pyridinium dichromate (7.2 g, 19.2 mmol) with stirring, and the resulting mixture was stirred at room temperature for 1 hour. After stirring, ether (250 ml) was added to the reaction mixture under stirring, and the resulting mixture was filtered with Celite. The filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:20) as the eluent to afford the title compound (2.0 g, yield: 70%) as a white crystalline solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. stirringAfter stirring
  3. stirringunder stirring
  4. filtrationthe resulting mixture was filtered with Celite
  5. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-3d4c3773359c44dc99f0e1abe6cf438b
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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