Reaction #956220

Reaction equation

4-Iodotetrahydropyran

4-bromobenzenethiol

potassium carbonate

→

sub-title compound

Yield 85.4%

4-(4-Bromophenyl)sulfanyltetrahydropyran

Yield 85.4%

Solvents

DMF

Et2O

Conditions

Workup

1. 1
   Washwashed with water (×2) and brine (×1)
2. 2
   DryingThe organic extracts was dried (MgSO4)
3. 3
   Concentrationconcentrated in vacuo
4. 4
   workup.ADDITIONPetroleum ether was added to the residue
5. 5
   Otherthe resultant precipitate removed by filtration
6. 6
   ConcentrationThe filtrate was concentrated in vacuo

Procedure

4-Iodotetrahydropyran (9 g, 42.45 mmol) was added to a stirred suspension of 4-bromobenzenethiol (7.296 g, 38.59 mmol) and potassium carbonate (10.67 g, 77.18 mmol) in DMF (15 mL) and the reaction stirred at ambient temperature for 3 hours. The mixture was diluted with Et2O and washed with water (×2) and brine (×1). The organic extracts was dried (MgSO4) and concentrated in vacuo. Petroleum ether was added to the residue and the resultant precipitate removed by filtration. The filtrate was concentrated in vacuo to give the sub-title compound as a light yellow oil (9.0 g, 85% Yield). 1H NMR (400.0 MHz, CDCl3) δ 1.63-1.73 (m, 2H), 1.89-1.93 (m, 2H), 3.23-3.30 (m, 1H), 3.45 (td, 2H), 3.99 (dt, 2H), 7.31 (d, 2H) and 7.45 (d, 2H) ppm.

Source