Hexane → 2,5-Difluoro-4-[(methylsulfinyl)(methylthio)methyl]benzonitrile
Reaction equation
[CH3:1][S:2]([CH2:4][S:5][CH3:6])=[O:3].C([Li])CCC.CCCCCC.[F:18][C:19]1[CH:26]=[C:25](F)[C:24]([F:28])=[CH:23][C:20]=1[C:21]#[N:22]>C1COCC1>[F:18][C:19]1[CH:26]=[C:25]([CH:4]([S:2]([CH3:1])=[O:3])[S:5][CH3:6])[C:24]([F:28])=[CH:23][C:20]=1[C:21]#[N:22]Participants
Conditions
- Temperature
- -78 °C
Procedure
(Methylsulfinyl)(methylthio)methane (3.16 g, 0.0255 mol) was dissolved in 50 mL of dry THF under argon and then cooled to −78° C. Butyllithium in hexane (16 mL 1.6M, 0.0256 mol) was added dropwise with stirring. The mixture was stirred for 15 min. Meanwhile a solution of 2,4,5-trifluorobenzonitrile (2.0 g; 0.013 mol) in 50 mL of dry THF was cooled to −78° C. under argon and the former solution was added through a cannula to the latter solution over a period of 3–5 min. After 30 min, the cooling bath was removed and when the reaction had reached room temperature it was poured into 200 mL of water. The THF was evaporated and the remaining aqueous layer was extracted three times with diethyl ether. The combined ether phase was washed with water, dried (Na2SO4) and evaporated. The crude product started to crystallise and could be used as such in the next step. Yield: 2.8 g (84%).
Workup
- stirringThe mixture was stirred for 15 min
- additionthe former solution was added through a cannula to the latter solution over a period of 3–5 min
- customthe cooling bath was removed
- customhad reached room temperature
- additionwas poured into 200 mL of water
- customThe THF was evaporated
- extractionthe remaining aqueous layer was extracted three times with diethyl ether
- washThe combined ether phase was washed with water
- dry with materialdried (Na2SO4)
- customevaporated
- customto crystallise
Sources & evidence
- ORD record
- ord-fa1d23c1ebdd48b8b8c9ea7a0e9959a4
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07129233B2
Reaction notes
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