Dimethylformamide → 3-(2-Bromoethoxy)-4-fluorobenzaldehyde
Reaction equation
[H-].[Na+].CN(C=O)C.[F:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[OH:17].[Br:18][CH:19](Br)[CH3:20]>C(OCC)(=O)C.O>[Br:18][CH2:19][CH2:20][O:17][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:9]=1[F:8])[CH:13]=[O:14]Participants
Conditions
- Temperature
- 140 °C
Procedure
Sodium hydride (1.14 g) was added to a DMF (30 mL) solution of 4-fluoro-3-hydroxybenzaldehyde (2.00 g) at room temperature, and the reaction solution was agitated for 30 minutes. Then, dibromoethane (2.46 mL) was added dropwise to the reaction solution, and the reaction solution was heated at 140° C. for 3 hours after the dropping ended. Water and ethyl acetate were added to the reaction solution under ice-cooling, and the organic layer was separated. The obtained organic layer was washed with a saturated sodium chloride solution, and the solvent was evaporated under reduced pressure after dried over anhydrous magnesium sulfate. The obtained residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate 6:1), and 606 mg (20%) 3-(2-bromoethoxy)-4-fluoro benzaldehyde was obtained. The physical properties of the compound are as follows.
Workup
- temperaturecooling
- customthe organic layer was separated
- washThe obtained organic layer was washed with a saturated sodium chloride solution
- customthe solvent was evaporated under reduced pressure
- dry with materialafter dried over anhydrous magnesium sulfate
- customThe obtained residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate 6:1)
Sources & evidence
- ORD record
- ord-e7bed0fbb3ee486896623e17711f7b50
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07880009B2
Reaction notes
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