Ethyl Acetate → 1-[2-Amino-3-chloro-4-(2,2-dimethoxy-ethoxy)-phenyl]-ethanone
Reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:19][O:20][CH:21]([O:24][CH3:25])[CH2:22]Br.CCOC(C)=O>CN(C=O)C.O>[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH2:22][CH:21]([O:24][CH3:25])[O:20][CH3:19])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
1-(2-Amino-3-chloro-4-hydroxyphenyl)ethanone (40 g, 215 mmol) was dissolved in DMF (360 ml). Cesium carbonate (140 g, 430 mmol) was added, followed by bromoacetaldehyde dimethyl acetal (54.5 g, 323 mmol). The mixture was then vigorously stirred at 65° C. for 24 h. Upon cooling to room temperature, EtOAc (1 L) and H2O (1 L) were added to the mixture. The organic layer was extracted with EtOAc (1×400 ml). The combined organic layer was washed with aqueous 3% LiCl solution (2×1 L), brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography to give 1-[2-amino-3-chloro-4-(2,2-dimethoxyethoxy)phenyl]-ethanone as a white solid (39 g, 67% yield).
Workup
- temperatureUpon cooling to room temperature
- extractionThe organic layer was extracted with EtOAc (1×400 ml)
- washThe combined organic layer was washed with aqueous 3% LiCl solution (2×1 L), brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-3d6471831bbe476c9e58b9a7f244e20e
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809267B2
Reaction notes
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