2-Bromopropane → HCID 20343306, compound
Reaction equation
[F:1][C:2]([F:16])([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]#[N:15])=[CH:9][CH:8]=1)[CH:3]([F:5])[F:4].Br[CH:18]([CH3:20])[CH3:19].[OH-].[Na+]>C1CC2OCCOCCOC3C(OCCOCCOC2CC1)CCCC3.C1C=CC=CC=1>[CH:18]([CH:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][C:2]([F:16])([F:1])[CH:3]([F:4])[F:5])=[CH:8][CH:9]=1)[C:14]#[N:15])([CH3:20])[CH3:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 45 °C
Procedure
A mixture of 39.85 g (0.171 mol) of p-(1,1,2,2-tetrafluoroethoxy)phenylacetonitrile, 3.71 g (9.96 mmol, 5.8 mol %) of dicyclohexyl-18-crown-6, 22.0 ml (28.8 g, 0.234 mol) of 2-bromopropane, 55 ml of benzene, and 55 ml of 50% sodium hydroxide is stirred for 45 minutes during which there is an exotherm from 25° C. to 43° C. The reaction mixture is then heated at 45° C. for 16.5 hours. After dilution with 200 ml of water, the reaction mixture is extracted with 200 ml of ether. The ether solution is washed with 400 ml of 12% hydrochloric acid, 200 ml of 5% hydrochloric acid, and 300 ml of water. The ether solution is dried with sodium sulfate, filtered, and then evaporated to give 47.13 g of an oil. This oil is vacuum distilled to give 34.83 g (74%), boiling point 83° C. to 85° C. at 0.055 to 0.090 mm Hg.
Workup
- customfrom 25° C. to 43° C
- extractionAfter dilution with 200 ml of water, the reaction mixture is extracted with 200 ml of ether
- washThe ether solution is washed with 400 ml of 12% hydrochloric acid, 200 ml of 5% hydrochloric acid, and 300 ml of water
- dry with materialThe ether solution is dried with sodium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-3e108a8b17f8451f9424f15af789e500
- Source dataset
- uspto-grants-1980_04
- Patent number
- US04199595
Reaction notes
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