2-Chloro-N-methoxy-N-methylacetamide → HCID 86708714, compound
Reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:14](I)=[CH:13][C:3]=1[CH2:4][O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].C([Mg]Cl)(C)C.[Cl-].[Li+].[Cl:25][CH2:26][C:27](N(OC)C)=[O:28]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:16]=[CH:15][C:14]([C:27](=[O:28])[CH2:26][Cl:25])=[CH:13][C:3]=1[CH2:4][O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]Participants
Procedure
To a solution of (2-bromo-5-iodobenzyloxy)-(tert-butyl)dimethylsilane (8.7 g, 20.3 mmol) in tetrahydrofuran (135 mL) under argon at −20° C. was added i-propylmagnesium chloride-lithium chloride solution (1.3M in THF, 16.4 mL, 21.3 mmol). After stirring at this temperature for thirty minutes, a solution of 2-chloro-N-methoxy-N-methyl acetamide (3.4 g, 24.3 mmol) in tetrahydrofuran (5 mL) was added to the reaction via cannula. The reaction was stirred at −20° C. for one hour and then warmed to room temperature. After one hour at room temperature the reaction was diluted with ethyl acetate and the organics were washed with saturated aqueous NH4Cl solution, water and brine. The organic layer was dried (MgSO4) and concentrated, and the resulting residue was purified by flash chromatography to yield 1-(4-bromo-3-((tert-butyldimethylsilyloxy)methyl)phenyl)-2-chloroethanone (5.1 g, 67%).
Workup
- stirringThe reaction was stirred at −20° C. for one hour
- washthe organics were washed with saturated aqueous NH4Cl solution, water and brine
- dry with materialThe organic layer was dried (MgSO4)
- concentrationconcentrated
- customthe resulting residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-e4fe50f47e604ad9bf927bd8129c7b9e
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156823B2
Reaction notes
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