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Diazonium salt 1 (14.1 mg, 0.0443 mmol) and 1,2,4-trimethoxybenzene (15.6 mg, 0.0928 mmol) were dissolved in 0.148 g of 95% aqueous ethanol. After 0.1 h, a red solid precipitated. After filtration the red solid was purified by SiO2 column chromatography (7:3 hexane/ethyl acetate) to give 27c as a red oil (12.8 mg, 72%): IR (ATR): {tilde over (v)}=2941, 1607, 1598, 1505, 1472, 1436, 1269, 1209, 1126, 1093, 1030, 839, 824 cm−1. MS (GC, EI): m/z=398 [M+], 140, 110. 1H NMR (500 MHz, CDCl3): δ=7.91 (d, J=9.0 Hz, 2H), 7.86 (d, J=9.0 Hz, 2H), 7.44 (s, 1H), 6.64 (s, 1H), 4.07 (s, 3H), 4.01 (s, 3H), 3.93 (s, 3H) ppm. 13C NMR (125 MHz, CDCl3): δ=154.74 (C), 154.70 (C), 154.3 (C), 154.0 (C), 144.1 (C), 135.1 (C), 126.9 (2CH), 122.4 (2CH), 98.8 (CH), 97.5 (CH), 57.6 (CH3), 56.22 (CH3), 56.17 (CH3) ppm. 19F NMR (470 MHz, CDCl3): δ=84.4 (quint, J=150 Hz, 1 F), 63.3 (d, J=150 Hz, 4 F) ppm.

1. customa red solid precipitated
2. filtrationAfter filtration the red solid
3. customwas purified by SiO2 column chromatography (7:3 hexane/ethyl acetate)