Thiophenol → 3-Bromopropyl phenyl sulfide

Participants

Reaction Steps

Powdered anhydrous potassium carbonate (4.3 kg, 31 moles) was added to a mixture of 1,3-dibromopropane (6.55 kg, 32 moles), thiophenol (1.2 kg, 10.9 moles) and methylethylketone (9 L). The alkylation was carried out under a hood in a 22 liter flask equipped with a mechanical stirrer, heating mantle, and 2 reflux condensers. Nitrogen gas was passed over the top of the condensers. Within 30 minutes the mixture had generated enough heat to attain reflux. Reflux was then maintained for another 30 to 60 minutes. The mixture was permitted to come to room temperature over an 18 hour period. The solvent layer was siphoned off and filtered through celite. The salts were filtered and washed with acetone. The filtrates were concentrated. The residue was vacuum distilled. Three fractions were collected:

Provenance & Evidence