18-Crown-6 → 2,3-Difluoro-6-(trifluoromethyl)benzonitrile
Reaction equation
Cl[C:2]1[C:3]([F:14])=[C:4]([C:7]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:9]=1)[C:5]#[N:6].[F-:15].[K+].C1OCCOCCOCCOCCOCCOC1>S1(CCCC1)(=O)=O>[F:14][C:3]1[C:2]([F:15])=[CH:9][CH:8]=[C:7]([C:10]([F:13])([F:12])[F:11])[C:4]=1[C:5]#[N:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 165 °C
Procedure
To a solution of 35.0 g of 3-chloro-2-fluoro-6-trifluoromethylbenzo nitrile in 200 ml of sulfolane was added 36.3 g of spray-dried potassium fluoride and 4.1 g of 18-crown-6-ether, and the mixture was stirred for 7 hours at 160-170° C. under a nitrogen atmosphere. After cooling, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer obtained was washed with saturated saline solution and then dried over anhydrous magnesium sulfate. Following to the concentration of the extract, the oily product obtained was distilled under reduced pressure to obtain 25.7 g of the title compound (bp. 98-100° C. (25 mmHg) nD 20.0-1.4413).
Workup
- temperatureAfter cooling
- extractionextracted with ethyl acetate
- customThe organic layer obtained
- washwas washed with saturated saline solution
- dry with materialdried over anhydrous magnesium sulfate
- customthe oily product obtained
- distillationwas distilled under reduced pressure
Sources & evidence
- ORD record
- ord-cd34eb997f964a22a9726af1114235d2
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06054605
Reaction notes
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