Cesium fluoride → HCID 18687737, compound

Participants

Reaction Steps

A stirred solution of 1-fluoro-3-isopropoxy-4-(trimethylsilyl)phenoxathiin (230 mg, 0.66 mmol) (Example 25) and CsF (200 mg, 1.32 mmol) in 5 mL 10% (v/v) aqueous DMF was heated under nitrogen at 100° C. for 0.5 h. After cooling to room temperature, the reaction was diluted with brine (30 mL), dried (Na2SO4), and concentrated in vacuo to a pale yellow oil (178 mg). Filtration of the crude product through silica gel (20 g) with 10% CH2Cl2 /hexanes yielded 142 mg (78%) of the title compound as a colorless oil: TLC (CH2Cl2 /hexanes, 10:90) Rf =0.31; 1H-NMR (CDCl3) d, J=6 Hz, 6 H), 4.43-4.47 (m, 1 H), d 6.36-6.41 (m, 2 H), C2 --H and C4 -H), d 6.95-7.14 (m, 4 H); MS m/e (relative intensity) 277 (MH+, 100).

Provenance & Evidence