Dimethylformamide → 2-Bromo-4-methoxy-3-(pentyloxy)benzaldehyde
Reaction equation
[Br:1][C:2]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O>[Br:1][C:2]1[C:9]([O:10][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
2-Bromo-3-hydroxy-4-methoxybenzaldehyde (225.2 g, 975 mmol) and DMF (660 ml) were mixed, and potassium carbonate (148.2 g, 1.07 mol) and bromopentane (133 ml, 1.07 mol) were successively added to this solution. The mixture was stirred at 90° C. for 1.5 hours and cooled to room temperature. Water (800 ml) was added to stop the reaction. The aqueous layer was extracted successively with diethyl ether (1000 ml, 500 ml) and ethyl acetate (500 ml). The organic layers were combined, washed successively with water (200 ml) and saturated brine (200 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give a crude product of 2-bromo4-methoxy-3-pentyloxybenzaldehyde.
Workup
- temperaturecooled to room temperature
- customthe reaction
- extractionThe aqueous layer was extracted successively with diethyl ether (1000 ml, 500 ml) and ethyl acetate (500 ml)
- washwashed successively with water (200 ml) and saturated brine (200 ml)
- dry with materialdried over anhydrous sodium sulfate
- filtrationThe drying agent was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d2c96e3b5092473cb15a8c3dafb1c06d
- Source dataset
- uspto-grants-2000_01
- Patent number
- US06017919
Reaction notes
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