Water → 5-Bromo-2-ethoxybenzaldehyde
Reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:18][CH3:19].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:18][CH3:19])=[C:6]([CH:9]=1)[CH:7]=[O:8]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
In DMF (150 ml) was dissolved 5-bromosalicylaldehyde (18.6 g). To the mixture was added at room temperature potassium carbonate (16.6 g) and then was added iodoethane (17.3 ml), and the mixture was stirred at 90° C. for 3 hours and cooled to room temperature. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=8/1) to give 5-bromo-2-ethoxybenzaldehyde (17.2 g).
Workup
- temperaturecooled to room temperature
- extractionthe mixture was extracted with ethyl acetate
- washwashed with saturated brine
- dry with materialdried with magnesium sulfate
- customUnder reduced pressure, the solvent was evaporated
- customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=8/1)
Sources & evidence
- ORD record
- ord-431c243198234839b6548416a23a3ec8
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06235771B1
Reaction notes
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