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

Temperatur

-23 °C

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).

1. customwas recooled to -78° C.
2. stirringThe reaction mixture was stirred for 3 h at ambient temperature
3. washwashed with aqueous ammonium chloride solution and brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. distillationThe residue was distilled

ORD-Eintrag

ord-3d8b557851dd4629afee23bc916f9121

Quelldatensatz

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05248677