Dimethylformamide → 2-Methyl-2-(4-(trifluoromethyl)phenyl)propanenitrile
Reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#N)=[CH:5][CH:4]=1.[H-].[Na+].CI.[CH2:18](OC(=O)C)C.C[N:25]([CH:27]=O)C>CCCCCC.O>[CH3:10][C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=1)([CH3:18])[C:27]#[N:25]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
(4-Trifluoromethyl-phenyl)-acetonitrile (1 g, 5.4010 mmol) in DMF (8.1 mL) was added to a stirred mixture of NaH (518.49 mg, 21.604 mmol) in DMF (8.1 mL) at 0° C. This was followed by the addition of methyl iodide (3.3 mL, 54.0102 mmol) and the resulting mixture was heated to 80° C. for 3 hours. The reaction was monitored by TLC (10% ethylacetate in hexane). The reaction mixture was diluted with cold water and extracted with diethyl ether. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 1.2 g of the crude product which was used in the next step without further purification.
Workup
- extractionextracted with diethyl ether
- washThe organic layer was washed with brine solution
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4b6eb69475b3491aaf06fdbd65ebdf46
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946260B2
Reaction notes
Loading…