Reaction #6486

Reaction equation

n-butyllithium

1,3-Dithiane

3-fluorobenzyl bromide

→

title compound

Yield 66.7%

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

Yield 66.7%

Solvents

hexane

methylene chloride

THF

Conditions

Workup

1. 1
   Otherwas recooled to -78° C.
2. 2
   workup.STIRRINGThe reaction mixture was stirred for 3 h at ambient temperature
3. 3
   Washwashed with aqueous ammonium chloride solution and brine
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   workup.DISTILLATIONThe residue was distilled

Procedure

1,3-Dithiane (12 g, 0.1 mol) was dissolved in 150 mL of anhydrous THF under a nitrogen atmosphere. The resultant solution was cooled to -78° C. and n-butyllithium (44 mL of a 2.5M solution of in hexane, 0.11 mol) was added. The reaction mixture was warmed to -23° C. and then stirred at -23° 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 diluted with methylene chloride, washed with aqueous ammonium chloride solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was distilled to afford 15.2 g (66.7% yield) of the title compound, b.p. 135°-140° C. (0.5 mm Hg); MS DCl--NH3M/Z: 229 (M+ H)+ ; 1H NMR (CDCl3) δ1.77-1.95 (1H, m), 2.05-2.18 (1H, m), 2.8-2.9 (4H, m), 3.02 (2H, d, J=7.5 Hz), 4.23 (1H, t, J=7.5 Hz), 6.9-7.1 (3H, m), 7.23-7.33 (1H, m).

Source