11-Bromo-1-undecene → 11-Bromo-1-undecanethiol

11-Bromo-1-undecanethiol was synthesized in two steps (see FIG. 11). First, 11-bromo-1-undecene (5.0 g) was converted to a thioacetate by reacting with AiBN (1.5 g) and thioacetic acid (10 mL) in toluene (50 mL). The reaction was run under Ar and refluxed for 2 h. The solution was washed with excess water and the toluene removed by rotary evaporation. The thioacetate was converted into a thiol by exposing the 11-bromo-1-undecanethioacetate to dry HCl. Acetyl chloride (6 mL) was added dropwise to dry methanol in an ice bath under Ar. The solution was allowed to warm to room temperature and the reaction progressed for approximately 6 h. Methylene chloride and water were added and the methylene chloride layer was washed several times with water. The solvent was removed by rotary evaporation.

1. temperaturerefluxed for 2 h
2. washThe solution was washed with excess water
3. customthe toluene removed by rotary evaporation
4. additionAcetyl chloride (6 mL) was added dropwise to dry methanol in an ice bath under Ar
5. additionMethylene chloride and water were added
6. washthe methylene chloride layer was washed several times with water
7. customThe solvent was removed by rotary evaporation

ORD record

ord-501926a45df84413a8afc8f04ef64956

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962029B2