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Diazonium salt 1 (11.9 mg, 0.0374 mmol) and 1,3,5-trimethoxybenzene (6.6 mg, 0.039 mmol) were dissolved in 0.18 g of 95% aqueous ethanol. After 0.1 h, a red solid precipitated which was filtered. The red precipitate was purified by SiO2 column chromatography (7:3 hexane/ethyl acetate) to afford 27b as a red oil (11.2 mg, 75%): IR (ATR): {tilde over (v)}=2943, 1599, 1456, 1335, 1207, 1151, 1126, 837 cm−1. MS (GC, EI): m/z=398 [M+], 271 [M+-SF5], 195, 152. 1H NMR (500 MHz, CDCl3): δ=7.91 (d, J=9.3 Hz, 2H), 7.85 (d, J=9.3 Hz, 2H), 6.23 (s, 2H), 3.93 (s, 6H), 3.92 (s, 3H) ppm. 13C NMR (125 MHz, CDCl3): δ=164.4 (C), 156.4 (2 C), 154.6 (C), 153.9 (C), 127.1 (C), 126.9 (2CH), 122.0 (2CH), 91.4 (2CH), 56.6 (2CH3), 55.7 (CH3) ppm. 19F NMR (470 MHz, CDCl3): δ=84.5 (quint, J=150 Hz, 1 F), 63.3 (d, J=150 Hz, 4 F) ppm.

1. customa red solid precipitated which
2. filtrationwas filtered
3. customThe red precipitate was purified by SiO2 column chromatography (7:3 hexane/ethyl acetate)