Dimethylformamide → 5-Cyano-2-fluorobenzaldehyde
Reaction equation
C(NC(C)C)(C)C.[F:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1.CN(C)[CH:19]=[O:20]>C1COCC1>[F:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=1[CH:19]=[O:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a stirred, cooled solution (0° C.) of diisopropylamine (15.4 mL, 0.11 mol) in anhydrous tetrahydrofuran (200 mL) n-butyllithium (40 mL of 2.5M in hexane, 0.11 mol) was added from a dropping funnel over a period of 30 min. under argon. The mixture was stirred at that temperature for 30 min. and then cooled to −78° C. A solution of 4-fluoro-benzonitrile (12.1g, 0.1 mol) in dry THF (50 mL) was then added dropwise over 15 min. via syringe and stirred for 1 hour at −78° C. Dimethylformamide (8 mL) was added dropwise from a syringe and the stirring was continued for another 20 min. The reaction was quenched by the rapid addition of acetic acid (20 mL) followed by water (500 mL) and the product was extracted with diethyl ether (2×500 mL). The combined organic layers were washed with 1N HCl, water, saturated sodium chloride and then dried over anhydrous magnesium sulfate, and evaporated to give 2-fluoro-5-cyano-benzaldehyde (11.8 g, 79% yield) as a light yellow solid.
Workup
- additionwas added from a dropping funnel over a period of 30 min. under argon
- stirringstirred for 1 hour at −78° C
- waitthe stirring was continued for another 20 min
- customThe reaction was quenched by the rapid addition of acetic acid (20 mL)
- extractionthe product was extracted with diethyl ether (2×500 mL)
- washThe combined organic layers were washed with 1N HCl, water, saturated sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-2067949aa9864a8ea159138cdaaa5fd8
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06221914B1
Reaction notes
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