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Table 7 Spectral data of synthesized bisarylic derivatives A1 to A5

From: gem-Difluorobisarylic derivatives: design, synthesis and anti-inflammatory effect

Compound 1H NMR 13C NMR (CDCl3, 75 MHz) 19F NMR (CDCl3, 282 MHz) HRMS (ESI)
A1 CDCl3, 300 MHz: 7.78 (m, 2H), 7.53 (m, 2H), 7.36 (t, 1H, J = 7.7 Hz), 7.17 (s, 1H), 3.77 (quad, 1H, J = 7.2 Hz), 3.51 (s, 3H), 2.36 (s, 3H), 2.33 (s, 3H), 1.51 (d, 3H, J = 7.2 Hz) CDCl3, 75 MHz: 197.0, 179.7, 166.7, 141.9, 140.2, 138.9, 138.7, 137.9, 132.0, 131.0, 129.2, 128.7, 128.6, 128.1, 126.8, 51.9, 45.1, 19.9, 19.6, 18.0   calcd. For C20H20O5Na: m/z [M + Na]+ 363.12029; found: 363.1203 (0 ppm); C20H19O5Na2: m/z [M-H + 2Na]+ 385.10224; found: 385.1014 (2 ppm).
A2 CDCl3, 300 MHz: 7.44–7.46 (m, 3H), 7.33–7.40 (m, 3H), 3.76 (quad, 1H, J = 7.1 Hz), 3.56 (s, 3H), 2.33 (s, 3H), 2.32 (s, 3H), 1.50 (d, 3H, J = 7.2 Hz) CDCl3, 75 MHz: 179.6, 168.5, 139.8, 139.7, 138.9, 138.3 (t, 2J = 27.7 Hz), 132.3 (t, 2J = 27.1 Hz), 130.8, 128.9 (t, 4J = 1.7 Hz), 128.7 (t, 3J = 3.4 Hz), 128.5 (2C), 125.2 (t, 3J = 5.1 Hz), 120.4 (t, 1J = 241.6 Hz), 68.3, 52.0, 45.2, 19.9, 19.4, 18.1 CDCl3, 282 MHz: – 82.30 (s) calcd. For C20H20F2O4Na: m/z [M + Na]+ 385.12219; found: 385.1223 (0 ppm); C20H19O4F2Na2: m/z [M + Na]+ 407.10413; found: 407.1045 (0 ppm).
A3 deuterated acetone, 300 MHz: 7.29–7.63 (m, 6H), 2.22 (s, 3H), 2.20 (s, 3H) deuterated acetone, 75 MHz: 170.0, 142.4 (t, 2J = 28.6 Hz), 141.7, 141.1 (t, 4J = 1.3 Hz), 134.6 (t, 3J = 1.7 Hz), 133.7 (t, 2J = 26.9 Hz), 132.7, 132.1, 131.3, 130.7 (t, 3J = 5.3 Hz), 130.0 (t, 3J = 8.0 Hz), 126.8 (t,3J = 5.3 Hz), 123.4, 122.0 (t, 1J = 241.6 Hz), 20.8, 20.4 CDCl3, 282 MHz:
− 82.34 (s)
calcd. For C16H13O2F 2 79 BrNa: m/z [M + Na]+ 376.99592; found: 376.9958 (0 ppm); C16H12O2F 2 79 BrNa2: m/z [M-H + 2Na]+ 398.97786; found: 398.9779 (0 ppm); C16H12O2F79BrNa: m/z [M-HF + Na]+ 356.98969; found: 356.9905 (2 ppm)
A4 deuterated acetone, 300 MHz: 8.18 (m, 1H), 8.07 (m, 1H), 7.77 (m, 1H), 7.56–7.61 (m, 3H), 2.60 (s, 3H), 2.39 (s, 3H), 2.36 (s, 3H) deuterated acetone, 75 MHz: 198.5, 170.0, 141.7, 141.1, 140.6 (t, 2J = 28.5 Hz), 138.9, 133.9 (t, 2J = 27.1 Hz), 132.6, 132.1 (t,3J = 7.5 Hz), 131.4, 131.1 (t, 4J = 3.4 Hz), 130.4, 130.0 (t, 3J = 7.9 Hz), 127.2 (t, 3J = 5.3 Hz), 122.5 (t, 1J = 241.7 Hz), 27.7, 20.8, 20.3 CDCl3, 282 MHz:
– 82.87 (s)
calcd. For C18H16O3F2Na: m/z [M + Na]+ 341.09597; found: 341.0960 (0 ppm)
A5 CDCl3, 300 MHz: 7.47 (s, 1H), 7.43 (s, 1H), 7.30 (s, 1H), 7.15–7.17 (m, 3H), 2.81 (sext., 1H, J = 6.9 Hz), 2.27 (s, 3H), 2.24 (s, 3H), 1.14 (d, 6H, J = 6.9 Hz) CDCl3, 75 MHz: 172.7, 148.7, 140.5, 138.6, 137.6 (t, 2J = 27.2 Hz), 133.6 (t, 2J = 27.7 Hz), 131.4, 128.8 (t, 3J = 7.8 Hz), 127.9 (2C), 127.7 (t, 4J = 1.6 Hz), 124.1 (t, 3J = 5.0 Hz), 123.6 (t, 3J = 5.2 Hz), 120.6 (t, 1J = 241.7 Hz), 34.1, 23.8 (2C), 19.9, 19.4 CDCl3, 282 MHz: –81.93 (s) calcd. For C19H20O2F2Na: m/z [M + Na]+ 341.13236; found: 341.1321 (1 ppm); C19H19O2FNa: m/z [M-HF + Na]+ 321.12613; found: 321.1260 (0 ppm); C19H19O2F2Na2: m/z [M-H + 2Na]+ 363.1143; found: 363.1157 (4 ppm); C19H20O2F2K: m/z [M + K]+ 357.10629; found: 357.1059 (1 ppm); C19H19O2: m/z [M-HF-F]+ 279.13796; found: 279.1379 (0 ppm)