Lithium cyanide → 4-Fluoro-3-iodobenzeneacetonitrile
Reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([I:10])[CH:4]=1.[C-:11]#[N:12].[Li+]>CN(C=O)C>[F:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:11]#[N:12])=[CH:4][C:5]=1[I:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
4-Bromomethyl-1-fluoro-2-iodo-benzene (33.8 g, 107 mMol) was added to 240 mL of a 0.5 M solution of lithium cyanide in DMF. The reaction mixture was heated to 80° C. under an atmosphere of dry N2 and stirred overnight at this temperature. The mixture was then cooled to ambient temperature and partitioned between Et2O and 0.1 N aqueous NaOH. The Et2O layer was then washed 4 more times with 0.1 N aqueous NaOH. The Et2O layer was then dried over MgSO4, filtered and concentrated under vacuum to give 24.7 g of the titled compound as a red solid which was used without purification.
Workup
- temperatureThe mixture was then cooled to ambient temperature
- custompartitioned between Et2O and 0.1 N aqueous NaOH
- washThe Et2O layer was then washed 4 more times with 0.1 N aqueous NaOH
- dry with materialThe Et2O layer was then dried over MgSO4
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-5599bcc2ee604bbfa7f07bf95c78ee4f
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06579887B2
Reaction notes
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