Diisopropylamine → 3-Chloro-2,6-difluorobenzaldehyde
Reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21].[CH:22](N1CCOCC1)=[O:23]>C1COCC1.Cl>[Cl:13][C:14]1[C:15]([F:21])=[C:16]([C:17]([F:20])=[CH:18][CH:19]=1)[CH:22]=[O:23]Participants
7
Conditions
- Temperature
- -78 °C
Procedure
n-Butyllithium (1.43M in hexane, 20.2 mmol, 14.1 ml) was added dropwise at 0° C. to a solution of diisopropylamine (2.91 ml, 22.2 mmol) in THF (80 ml). After 30 min. at 0° C., the solution was cooled to -78° C. and 1-chloro-2,4-difluorobenzene (3 g, 20.2 mmol) in THF (10 ml) added dropwise. After 30 min., 4-formylmorpholine (4.1 ml) was added and the mixture warmed to room temperature over 1 h, diluted with 1N HCl, extracted twice with ethyl acetate, the extracts washed with brine, dried over sodium sulphate and evaporated to give a mobile yellow oil (2.2 g), MS (+EI) 178/177/176/175 (M+), 1H NMR (CDCl3) 10.34 (1H, s), 7.66-7.60 (1H, m), 7.00 (1H, dt, J6.9 Hz, 1.2 Hz).
Workup
- waitAfter 30 min.
- temperaturethe mixture warmed to room temperature over 1 h
- extractionextracted twice with ethyl acetate
- washthe extracts washed with brine
- dry with materialdried over sodium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-8e338ddf3150493d8c323bb3a2d333e9
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05883102
Reaction notes
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