Water → 3-(2-Bromo-4,5-dimethoxyphenyl)propanenitrile
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1C(=O)N([Br:22])C(=O)C1.O>CN(C=O)C>[Br:22][C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:11][CH2:12][C:13]#[N:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 1 g (5.3 mmoles) of 3-(3,4-dimethoxyphenyl)propanenitrile in 42 mL of DMF is cooled to 0° C. To the resulting solution there is added, little by little, 0.93 g of NBS (5.2 mmoles, 1 eq.). After stirring for 30 minutes at 0° C., the reaction mixture is brought back to ambient temperature and stirred for two hours. It is then hydrolysed using 170 mL of water and extracted twice with 130 mL of ethyl acetate. The organic phases are collected and then washed, first with saturated aqueous Na2S2O5 solution and then with water. After evaporating off the solvent under reduced pressure, 1.29 g of a colourless oil which crystallises into a white solid are obtained.
Workup
- additionTo the resulting solution there is added
- customis brought back to ambient temperature
- stirringstirred for two hours
- extractionextracted twice with 130 mL of ethyl acetate
- customThe organic phases are collected
- washwashed, first with saturated aqueous Na2S2O5 solution
- customAfter evaporating off the solvent under reduced pressure, 1.29 g of a colourless oil which
- customcrystallises into a white solid
- customare obtained
Sources & evidence
- ORD record
- ord-a655c0a9287149348456602ed37746f2
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08779121B2
Reaction notes
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