1-Bromopentane → 2-Phenylheptanenitrile
Reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>CN(C=O)C>[C:1]1([CH:7]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
5 g (42.7 mmol) of phenylacetonitrile are added dropwise to a suspension of 2 g of 60% NaH in 50 ml of DMF cooled to 0° C. 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 ambient temperature and then treated with ice and extracted with ethyl ether. The organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over sodium sulphate, filtered and evaporated under pressure. An orangey-yellow oil is obtained and purified by fractionated distillation under reduced pressure (70-75° C. under 1×10−1 mbar). 5.14 g in the form of an orangey oil are obtained with a yield of 64%.
Workup
- stirringThe reaction medium is stirred for 16 hours at ambient temperature
- additiontreated with ice
- extractionextracted with ethyl ether
- washThe organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate
- dry with materialdried over sodium sulphate
- filtrationfiltered
- customevaporated under pressure
- customAn orangey-yellow oil is obtained
- distillationpurified by fractionated distillation under reduced pressure (70-75° C. under 1×10−1 mbar)
- custom5.14 g in the form of an orangey oil are obtained with a yield of 64%
Sources & evidence
- ORD record
- ord-d8c9f7c69aa44e8db8cfdbd2105b8638
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871187B2
Reaction notes
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