Hydrochloric Acid → 1-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)cyclopropane-1-carbonitrile
Reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:5]([CH2:14][C:15]#[N:16])=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.Cl.Br[CH2:19][CH2:20]Cl>O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:3][C:4]1[C:5]([C:14]2([C:15]#[N:16])[CH2:20][CH2:19]2)=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:11])[F:12])[CH:9]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
2.90 g of Sodium hydroxide was dissolved in 10 ml of water and 1.94 g of benzyltriethylammonium chloride was added at ambient temperature. The solution was stirred and a solution of 2.00 g of (3-chloro-5-trifluoromethyl-pyridin-2-yl)-acetonitrile in 2.8 ml of 1-bromo-2-chloroethane was added dropwise. The reaction mixture was stirred at 60° C. for 3 h. The reaction mixture was then cooled to 0° C. and acidified to pH1 with concentrated aqueous hydrochloric acid (36%). The reaction mixture was extracted twice with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. Thus, 2.09 g of crude 1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropanecarbonitrile was obtained as a brown oil, which was used for the next step without further purification. 1H-NMR (CDCl3): 8.68 ppm (s, 1H), 8.00 ppm (s, 1H), 1.80 ppm (m, 2H), 1.70 ppm (m, 2H).
Workup
- stirringThe reaction mixture was stirred at 60° C. for 3 h
- extractionThe reaction mixture was extracted twice with ethyl acetate
- washThe organic phase was washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d545e35068624dca87cee5af094e944b
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040708B2
Reaction notes
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