1-Bromopentane → 2-Phenylheptanenitrile
Reaction equation
[H-].[Na+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>CN(C=O)C>[C:3]1([CH:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of 2 g of 60% NaH in 50 mL of DMF cooled to 0° C. are added dropwise 5 g (42.7 mmol) of phenylacetonitrile. After stirring for 30 minutes at 0° C., 5.32 mL (42.7 mmol) of bromopentane are added dropwise. The reaction medium is stirred for 16 hours at room temperature and then treated with ice and extracted with ethyl ether. The organic phase is washed with saturated aqueous sodium hydrogen carbonate solution, dried over sodium sulfate, filtered and evaporated under pressure. An orange-yellow oil is obtained and purified by fractional distillation under reduced pressure (70-75° C. at 1×10−1 mbar). 5.14 g in the form of an orange-coloured oil are obtained in a yield of 64%.
Workup
- stirringThe reaction medium is stirred for 16 hours at room temperature
- additiontreated with ice
- extractionextracted with ethyl ether
- washThe organic phase is washed with saturated aqueous sodium hydrogen carbonate solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated under pressure
- customAn orange-yellow oil is obtained
- distillationpurified by fractional distillation under reduced pressure (70-75° C. at 1×10−1 mbar)
- custom5.14 g in the form of an orange-coloured oil are obtained in a yield of 64%
Sources & evidence
- ORD record
- ord-b8c699b5bac942dfa635d89a2552b483
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877968B2
Reaction notes
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