Реакция #6487

Уравнение реакции

n-butyllithium

1,3-Dithiane

THF

3-fluorobenzyl bromide

→

title compound

Выход 94.0%

2-(4-Fluorophenyl)methyl-1,3-dithiane

Выход 94.0%

Растворители

hexane

Условия реакции

Обработка

1. 1
   Другоеwas recooled to -78° C.
2. 2
   workup.STIRRINGThe reaction mixture was stirred for 3 h at ambient temperature
3. 3
   Другоеthe reaction was quenched with aqueous ammonium chloride solution
4. 4
   ДругоеThe layers were separated
5. 5
   Экстракцияthe aqueous layer was extracted with ethyl acetate
6. 6
   СушкаThe combined organic extracts were dried over anhydrous magnesium sulfate
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated under reduced pressure
9. 9
   workup.DISTILLATIONThe residue was distilled

Методика

1,3-Dithiane (20 g, 166 mmol) was dissolved in 250 mL of anhydrous THF under a nitrogen atmosphere. The resultant solution was cooled to -78° C. and n-butyllithium (128 mL of a 1.5M solution of in hexane, 199 m mol) was added. The reaction mixture was warmed to 0° C. and then stirred at 0° C. for 0.5 h. The reaction mixture was recooled to -78° C. and 25 g (0.135 mol) of 3-fluorobenzyl bromide was added over a 15 minute period. The reaction mixture was stirred for 3 h at ambient temperature and then the reaction was quenched with aqueous ammonium chloride solution. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was distilled to afford 35.5 g (94% yield) of the title compound, b.p. 125°-145° C. (0.75 mm Hg); MS DCl--NH3M/Z: 229 (M+H)+ ; 1H NMR (CDCl3) δ1.76-1.95 (1H, m), 2.05-2.19 (1H, m), 2.78-2.98 (4H, m), 2.99 (2H, d, J=9 Hz), 4.21 (1H, t, J=9 Hz), 6.93-7.05 (2H, m), 7.16-7.25 (2H, m).

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