Reaction equation
[CH2:1]([C:4]1[C:9]([Cl:10])=[C:8]([Cl:11])[CH:7]=[CH:6][C:5]=1[OH:12])[CH2:2][CH3:3].O1CCCC1.BrC[CH2:20][CH2:21][CH2:22][C:23]#[N:24].[H-].[Na+]>O.C(OCC)(=O)C.CN(C)P(N(C)C)(N(C)C)=O>[CH2:1]([C:4]1[C:9]([Cl:10])=[C:8]([Cl:11])[CH:7]=[CH:6][C:5]=1[O:12][CH2:20][CH2:21][CH2:22][C:23]#[N:24])[CH2:2][CH3:3]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 65 °C
Procedure
To a solution of 37.1 g. of 2-propyl-3,4-dichlorophenol in 400 ml. of dry tetrahydrofuran and 25 ml. of hexamethylphosphoramide were added 32 ml. of 5-bromovaleronitrile. Sodium hydride (7.2 g. of a 60% dispersion in mineral oil) was added and the reaction was stirred for about three days at 65° C. The reaction mixture was cooled to room temperature and ethyl acetate and water were added. The solution was evaporated and ethyl acetate and water were added. The layers were separated and the ethyl acetate was washed several times with dilute hydrochlorid acid. The organic layer was filtered through sodium sulfate and evaporated to provide the desired nitrile intermediate. NMR.
Workup
- additionof a 60% dispersion in mineral oil) was added
- temperatureThe reaction mixture was cooled to room temperature
- customThe solution was evaporated
- additionethyl acetate and water were added
- customThe layers were separated
- washthe ethyl acetate was washed several times with dilute hydrochlorid acid
- filtrationThe organic layer was filtered through sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-926f1687b0174b80a0cedf65e944a367
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04764521
Linked notes
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