Iodine → 1,3-Dithiolane, 2-(p-chlorophenyl)-2-methyl-

A mixture of 4-chloroacetophenone (1.3 mL, 10 mmol), iodine (250 mg, 1 mmol), 1,2-ethanedithiol (0.85 mL, 10 mmol) in dry tetrahydrofuran (20 mL) was heated at reflux under an atmosphere of nitrogen for 16 h. The mixture was allowed to cool to room temperature and concentrated in vacuo and the residue taken up in ether (20 mL). The organic solution was washed with water (2×10 mL) and brine (1×10 mL), then dried (Na2SO4) and evaporated under reduced pressure. Flash column chromatography of the residue, eluting with 37% aqueous ammonia:ether:hexane (0.02:1:6) afforded 2-(4-chlorophenyl)-2-methyl-1,3-dithiolane (24) as a colourless oil (1.11 g, 48%). 1H nmr (300 MHz, CDCl3) 2.13 (s, 3H, CH3), 3.31-3.53 (m, 4H, SCH2CH2S), 7.27 (d, J=8.7 Hz, 2H, 2×ArH), 7.69 (d, J=8.7 Hz, 2H, 2×ArH).

1. temperaturewas heated
2. temperatureat reflux under an atmosphere of nitrogen for 16 h
3. concentrationconcentrated in vacuo
4. washThe organic solution was washed with water (2×10 mL) and brine (1×10 mL)
5. dry with materialdried (Na2SO4)
6. customevaporated under reduced pressure
7. washFlash column chromatography of the residue, eluting with 37% aqueous ammonia:ether:hexane (0.02:1:6)

ORD record

ord-ef86a2f5be30482fa431f2dc53213116

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863313B2