Isopropyl iodide → 5-Ethoxy-2-fluoro-3-isopropoxybenzaldehyde
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([OH:13])[C:7]([F:12])=[C:8]([CH:11]=1)[CH:9]=[O:10])[CH3:2].C([O-])([O-])=O.[K+].[K+].I[CH:21]([CH3:23])[CH3:22]>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:13][CH:21]([CH3:23])[CH3:22])[C:7]([F:12])=[C:8]([CH:11]=1)[CH:9]=[O:10])[CH3:2]Participants
5
Conditions
- Temperature
- 50 °C
Procedure
To a solution of Intermediate 7.1 (assumed 24.3 mmol) in 50 mL DMF, was added K2CO3 (4.03 g, 29.2 mmol) and 2-iodopropane (4.86 mL, 48.6 mmol). The mixture was stirred at 50° C. for 16 h, then was diluted with EtOAc/hexanes (1:1). The organic phase was washed with H2O (3×) and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 30% EtOAc/hexanes gradient) to afford 3.94 g of Intermediate 7.2 as a white solid.
Workup
- washThe organic phase was washed with H2O (3×) and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe crude product was purified by flash chromatography (0 to 30% EtOAc/hexanes gradient)
Sources & evidence
- ORD record
- ord-7e3e269b95034331b0f1e4fbcf9e514e
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576098B2
Reaction notes
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