benzofuran-4-yl trifluoromethanesulfonate synthesis
- Product Name:benzofuran-4-yl trifluoromethanesulfonate
- CAS Number:177734-79-1
- Molecular formula:C9H5F3O4S
- Molecular Weight:266.19
Yield:177734-79-1 76%
Reaction Conditions:
with pyridine;dmap in dichloromethane at 0; for 2 h;
Steps:
4.1.2.5. 1-(Benzofuran-4-yl)-3-(dimethylamino)propan-1-one (classD-4). A solution of benzofuran-4-ol (2.61 g, 19.5 mmol), DMAP(0.060 g, 0.49 mmol) and pyridine (2.37 mL, 29.3 mmol) in DCM(60 mL, anhydrous) at 0 C was treated with TFAA (4.92 mL, 29.2mmol) and then stirred at 0 C for 2 h. The mixture was partitionedbetween DCM and water; the organic fractions were dried andevaporated. Column chromatography (hexanes) gave benzofuran-4-yl trifluoromethanesulfonate (3.93 g, 76%). 1H NMR (CDCl3) d7.70 (d, J = 2.3 Hz, 1H), 7.56 (d, J = 8.2 Hz, 1H), 7.35 (t, J = 8.2 Hz,1H), 7.20 (d, J = 8.1 Hz, 1H), 6.90 (dd, J = 1.9, 1.0 Hz, 1H). Found:[M+H] = 267.0.
References:
Sutherland, Hamish S.;Tong, Amy S.T.;Choi, Peter J.;Conole, Daniel;Blaser, Adrian;Franzblau, Scott G.;Cooper, Christopher B.;Upton, Anna M.;Lotlikar, Manisha U.;Denny, William A.;Palmer, Brian D. [Bioorganic and Medicinal Chemistry,2018,vol. 26,# 8,p. 1797 - 1809]
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