Hydrochloric Acid → 3,5-Dibromobenzaldehyde
Reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([Br:13])[CH:10]=[C:9]([Br:14])[CH:8]=1.CN(C)[CH:17]=[O:18].Cl>CCCCCC.C(OCC)C>[Br:14][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([Br:13])[CH:10]=1)[CH:17]=[O:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -80 °C
Procedure
0.222 mol of a solution of n-butyllithium in hexane is added dropwise at −80° C. to 0.222 mol of 1,3,5-tribromobenzene in 1.8 liters of ethyl ether. The reaction mixture is stirred at −80° C. for one hour. A solution of 0.222 mol of N,N-dimethylformamide in 50 ml of ethyl ether is slowly added. The temperature is maintained at −80° C. for one hour, before being brought to ambient temperature. Stirring is carried out for one night. 450 ml of 1N hydrochloric acid are added. The reaction mixture is extracted with ether. The organic phases are collected and dried over magnesium sulphate. After filtration and removal of the solvents by evaporation, the crude product is purified by chromatography on a silica column (eluant: cyclohexane/ethyl acetate: 95/5).
Workup
- temperatureThe temperature is maintained at −80° C. for one hour
- custombefore being brought to ambient temperature
- stirringStirring
- waitis carried out for one night
- extractionThe reaction mixture is extracted with ether
- customThe organic phases are collected
- dry with materialdried over magnesium sulphate
- filtrationAfter filtration and removal of the solvents
- customby evaporation
- customthe crude product is purified by chromatography on a silica column (eluant: cyclohexane/ethyl acetate: 95/5)
Sources & evidence
- ORD record
- ord-72bdab3066444a1a9a3d49eb99d0d51f
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06541471B1
Reaction notes
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