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Synthesis of aryl ethers via a sulfonyl transfer reaction.

Organic letters (2012-07-18)
Neal W Sach, Daniel T Richter, Stephan Cripps, Michelle Tran-Dubé, Huichun Zhu, Buwen Huang, Jean Cui, Scott C Sutton
ABSTRACT

A general synthesis of aryl ethers from primary and secondary alcohols and aryl mesylates is presented. The reaction proceeds via a sulfonyl-transfer mechanism. In this paper, we compare the sulfonyl transfer reaction to Mitsunobu ether formation. The reaction can be employed in a multistep synthesis where the aryl mesylate is used as a phenol protecting group and then as an activating group for ether formation. This protecting/activating group strategy is demonstrated using raloxifene as the target.

MATERIALS
Product Number
Brand
Product Description

Supelco
Methanesulfonic acid concentrate, 0.1 M CH3SO3H in water (0.1N), eluent concentrate for IC
Sigma-Aldrich
Methanesulfonic acid solution, 70 wt. % in H2O
Sigma-Aldrich
Silver methanesulfonate
Sigma-Aldrich
Methanesulfonic acid, ≥99.0%
Sigma-Aldrich
Methanesulfonic acid solution, 4 M (with 0.2% (w/v) tryptamine)
Sigma-Aldrich
Potassium methanesulfonate, ≥98.0% (dry substance, T)
Sigma-Aldrich
Sodium methanesulfonate, 98%