Alcohol to a leaving group (OTs, OMs)

 
   
 

The alcohol can be converted into a good leaving group by reacting with mesyl chloride (MsCl) or tosyl chloride (TsCl) in the presence of base.

Mechanism

  • The alcohol performs a substitution reaction on sulfur, causing the formation of an O-S bond and the breaking of the S-Cl bond.
  • Subsequently, deprotonation of the positively charged alcohol leads to the neutral mesylate or tosylate.