Reaction #1810822

Reaction equation

2-chloro-5-methanesulfonyl-benzoic acid

2,2,2-trifluoro-ethanol

→

title compound

5-methanesulfonyl-2-(2,2,2-trifluoro-ethoxy)-benzoic acid

Solvents

NEt3

Conditions

Workup

1. 1
   OtherThe volatiles were removed under vacuum
2. 2
   ExtractionExtraction with ethyl acetate
3. 3
   Otherdrying of the combined organic fractions and evaporation
4. 4
   Otheryielded a residue which
5. 5
   Otherwas purified by reversed phase preparative HPLC
6. 6
   Washeluting with an acetonitrile/water gradient
7. 7
   OtherEvaporation of the product fractions

Procedure

A mixture of 2.13 mmol 2-chloro-5-methanesulfonyl-benzoic acid, 0.64 mmol Cu(I)Br in 5 ml NEt3 and 25 ml 2,2,2-trifluoro-ethanol was heated to 120° C. for 16 h in a sealed tube. The volatiles were removed under vacuum and the residue was taken up in 70 ml 1N HCl. Extraction with ethyl acetate drying of the combined organic fractions and evaporation yielded a residue which was purified by reversed phase preparative HPLC eluting with an acetonitrile/water gradient. Evaporation of the product fractions yielded the title compound. MS (m/e): 297.0 (M−H, 100%)

Source