Potassium Carbonate → 2-(4-Bromophenyl)propanenitrile
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[CH3:11]OC(=O)OC.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]([CH3:11])[C:7]#[N:8])=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 180 °C
Procedure
An autoclave is charged with 25.0 g (128 mmol) 4-bromobenzylcyanide, 190 mL dimethylcarbonate and 0.900 g (6.51 mmol) K2CO3 and stirred for 16 h at 180° C. Then the reaction mixture is allowed to cool to r.t., the mixture is diluted with EtOAc and washed with water (1×), aq. 10% Na2S2O3 solution (1×) and brine (1×). The organic layer is dried with MgSO4 and the solvent is removed in vacuo. The residue is purified by destillation (bath temperature 204° C., head temperature 153° C.).
Workup
- temperatureto cool to r.t.
- washwashed with water (1×), aq. 10% Na2S2O3 solution (1×) and brine (1×)
- dry with materialThe organic layer is dried with MgSO4
- customthe solvent is removed in vacuo
- customThe residue is purified by destillation (bath temperature 204° C., head temperature 153° C.)
Sources & evidence
- ORD record
- ord-f061d94d1d1049f98482bce5df7fa9f7
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08835472B2
Reaction notes
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