Diethylamine → 4-(Diethylamino)-3-(trifluoromethyl)benzonitrile
Reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15].C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[CH2:14]([N:16]([CH2:17][CH3:18])[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11])[CH3:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 135 °C
Procedure
A mixture of 4-bromo-3-(trifluoromethyl)-benzonitrile (Yonezawa et al., Synthetic Communications (1996), 26, 1575-1578; 6.0 g, 24 mmol), diethylamine (8.3 mL, 80 mmol) and 25 mL N,N-dimethylacetamide is stirred in a tightly closed vessel for 16 hours at 135° C. After cooling, the reaction mixture is treated with a half-saturated aqueous solution of sodium hydrogen carbonate and extracted three times with ethyl acetate. The combined organic extracts are dried (Na2SO4) and the solvent is evaporated off under reduced pressure. The crude product is purified by column chromatography on silica gel, eluent hexane/ethyl acetate to give the title compound as an orange oil.
Workup
- temperatureAfter cooling
- extractionextracted three times with ethyl acetate
- dry with materialThe combined organic extracts are dried (Na2SO4)
- customthe solvent is evaporated off under reduced pressure
- customThe crude product is purified by column chromatography on silica gel, eluent hexane/ethyl acetate
Sources & evidence
- ORD record
- ord-dece2e21328944b8b1c8f36a9cc25562
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07655669B2
Reaction notes
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