N-Formylmorpholine → 5-(Dimethoxymethyl)-2-fluorobenzaldehyde
Reaction equation
Br[C:2]1[CH:7]=[C:6]([CH:8]([O:11][CH3:12])[O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[F:13].C([Li])CCC.[CH:19](N1CCOCC1)=[O:20].[Cl-].[NH4+]>O1CCCC1.CCCCCC.O>[CH3:10][O:9][CH:8]([O:11][CH3:12])[C:6]1[CH:5]=[CH:4][C:3]([F:13])=[C:2]([CH:7]=1)[CH:19]=[O:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -60 °C
Procedure
6.2 g of 2-Bromo-4-dimethoxymethyl-1-fluorobenzene was dissolved in 65 ml of tetrahydrofuran, and the solution was cooled to −60° C. under a nitrogen gas flow. 18 ml of 1.6M n-Butyl lithium in hexane was added dropwise and the mixture was stirred at −60° C. for 1 hour. 3.3 ml of N-Formylmorpholine was added thereto, and the reaction mixture was allowed to warm to room temperature. The mixture was stirred for 1 hour, then ice-cooled, and treated with water and ammonium chloride solution, then extracted with ethylacetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was subjected to silica gel column chromatography, to give 2.8 g of the title compound (8% ethyl acetate-hexane).
Workup
- temperatureto warm to room temperature
- stirringThe mixture was stirred for 1 hour
- temperatureice-cooled
- extractionextracted with ethylacetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-8b403390309646caa5dcc6ba0835f738
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07544835B2
Reaction notes
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