Dimethylformamide → 5-Chloro-2-fluorobenzaldehyde
Reaction equation
C([Li])CCC.CC1(C)CCCC(C)(C)N1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1.CN(C)[CH:26]=[O:27]>CCCCCC.O1CCCC1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[C:19]([CH:18]=1)[CH:26]=[O:27]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1.6M butyllithium in hexane (32 ml) was added anhydrous tetrahydrofuran (100 ml), and then added dropwise 2,2,6,6-tetramethylpiperidine (8.4 ml) at −70° C. or less. To the mixture was added dropwise a solution of 1-chloro-4-fluorobenzene (6.5 g) in anhydrous tetrahydrofuran (20 ml), and the mixture was stirred at −70° C. or less for 2 hours. To the mixture was added dropwise a solution of dimethylformamide (6.5 g) in tetrahydrofuran (15 ml), and the mixture was allowed to stand to warm up to 0° C. The reaction solution was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give oil of 5-chloro-2-fluorobenzaldehyde (5.1 g).
Workup
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water and saturated brine
- dry with materialdried with magnesium sulfate
- customUnder reduced pressure, the solvent was evaporated
Sources & evidence
- ORD record
- ord-b386910a3ba54cef97117322479752e3
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06350749B1
Reaction notes
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