Sodium Cyanide → 2-(4-Chloro-3-(trifluoromethyl)phenyl)acetonitrile
Reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([C:10]([F:13])([F:12])[F:11])[CH:4]=1.[C-:14]#[N:15].[Na+]>CS(C)=O>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:14]#[N:15])=[CH:4][C:5]=1[C:10]([F:13])([F:12])[F:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
3.94 g of 4-bromomethyl-1-chloro-2-trifluoromethyl-benzene (14.4 mmol) and 1.06 g sodium cyanide (21.6 mmol) were suspended in 12 ml DMSO under argon and stirring and heated to 50° C. for 1 h. The reaction mixture was then poured on water/ice and extracted four times with DCM. The combined organic phases were washed with water, dried with magnesium sulfate, filtered and concentrated in vacuo, leading to 3.188 g of (4-chloro-3-trifluoromethyl-phenyl)-acetonitrile as a dark red oil, which was directly used in the next step.
Workup
- additionThe reaction mixture was then poured on water/ice
- extractionextracted four times with DCM
- washThe combined organic phases were washed with water
- dry with materialdried with magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-fd24342902984c1ba50b0f772d0de7ed
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07678818B2
Reaction notes
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