Diethyl Ether → 4-Bromo-2-chlorobenzaldehyde
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- stirringthe resulting mixture was stirred at room temperature for 1 hour
- stirringAfter stirring
- stirringunder stirring
- filtrationthe resulting mixture was filtered with Celite
- 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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