What is the best choice of reagent to achieve the following transformation?

Question

Quizplus · Accepted Answer

The transformation involves replacing the hydroxyl group (-OH) with a chloro group (-Cl) on the aromatic ring. This is best achieved by using a reagent that can convert the hydroxyl group to a good leaving group, such as a mesylate or a tosylate. In this case, thionyl chloride (SOCl2) is used to convert the hydroxyl group to a chlorosulfite intermediate, which is then attacked by the pyridine to form the final product. HCl and HOCl are not strong enough to convert the hydroxyl group to a good leaving group, and Cl₂, light is not a known reagent.

What Is the Best Choice of Reagent to Achieve the Following