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Table 5 Spectral data of intermediates 4–18

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

Compound

1H NMR

13C NMR

19F NMR

4

CDCl3, 300 MHz: 7.56 (m, 1H), 7.36 (m, 2H), 7.18 (m, 1H), 5.44 (s, 1H), 3.70 (s, 3H), 3.64 (br. s, 1H)

CDCl3, 75 MHz: 153.7, 140.5, 131.8, 130.2, 129.6, 125.1, 122.7, 86.0, 77.6, 63.2, 53.0

 

5

CDCl3, 300 MHz: 8.02 (t, 1H, J = 1.7 Hz), 7.86 (ddd, 1H, J = 7.9, 1.7 and 1.0 Hz), 7.61 (ddd, 1H, J = 7.9, 1.7 and 1.0 Hz), 7.23 (t, 1H, J = 7.9 Hz), 3.73 (s, 3H)

CDCl3, 75 MHz: 173.6, 151.4, 137.0, 136.1, 131.3, 129.5, 127.4 (3C), 79.7, 78.3, 52.6.

 

6

CDCl3, 300 MHz: 8.01 (t, 1H, J = 1.9 Hz), 7.80 (m, 1H), 7.68 (m, 1H), 7.33 (t, 1H, J = 7.8 Hz), 3.53 (s, 3H), 2.97–2.98 (m,4H), 1.74 (s, 3H), 1.67 (s, 3H)

CDCl3, 75 MHz: 197.1, 165.9, 146.8, 137.0, 136.0, 131.2, 130.3, 127.1, 125.6, 123.1, 123.0, 120.6, 51.8, 36.5, 32.6, 18.2, 17.8

 

7

CDCl3, 300 MHz: 7.89 (t, 1H, J = 1.7 Hz). 7.81 (s, 1H), 7.62 (m, 2H), 7.27 (t, 1H, J = 7.9 Hz), 7.13 (s, 1H), 3.61 (s, 3H), 2.36 (s, 3H), 2.33 (s, 3H)

CDCl3, 75 MHz: 195.9, 166.3, 142.1, 139.3, 138.8, 138.6, 135.6, 131.8, 131.1, 129.9, 128.8, 127.7, 126.4, 122.7, 52.0, 19.9, 19.6

 

8

CDCl3, 300 MHz: 7.70 (s, 1H), 7.55 (m, 1H), 7.49 (m, 1H), 7.26 (t, 1H, J = 8.0 Hz), 3.76 (s, 3H)

CDCl3, 75 MHz: 152.1 (t, 4J = 2.4 Hz), 136.2 (t, 2J = 27.5 Hz), 134.5 (t, 4J = 1.6 Hz), 130.4, 128.3 (t, 3J = 5.0 Hz), 123.9 (t, 3J = 4.9 Hz), 122.7, 110.4 (t, 1J = 236.3 Hz), 78.4 (t, 3J = 5.9 Hz), 76.5 (t, 2J = 43.7 Hz), 53.4 

CDCl3, 282 MHz: -80.06 (s)

9

CDCl3, 300 MHz: 7.70 (s, 1H), 7.50 (s, 1H), 7.48 (s, 1H), 7.23 (m, 1H), 3.68 (s, 3H), 2.86 (t, 2H, J = 7.2 Hz), 2.50 (t, 2H, J = 7.2 Hz), 1.57 (s, 3H), 1.52 (s, 3H)

CDCl3, 75 MHz: 170.3, 137.7 (t, 2J = 28.4 Hz), 133.2, 130.0, 129.9 (t, 3J = 5.0 Hz), 128.9 (t, 3J = 5.9 Hz), 128.8 (t, 2J = 25.4 Hz), 124.5 (t, 4J = 5.6 Hz), 122.5, 121.6, 121.2, 119.4 (t, 1J = 244.4 Hz), 52.1, 35.8, 31.6, 18.0, 17.7

CDCl3, 282 MHz: − 93.06 (s)

10

CDCl3, 300 MHz: 7.62 (s, 1H), 7.54 (m, 1H), 7.49 (s, 1H), 7.47 (s, 1H), 7.40 (m, 1H), 7.26 (m, 1H), 3.65 (s, 3H), 2.36 (s, 3H), 2.33 (s, 3H)

CDCl3, 75 MHz: 168.2, 140.1 (t, 2J = 28.3 Hz), 140.0, 139.1 (t, 4J = 1.3 Hz), 132.8 (t, 4J = 2.7 Hz), 131.9 (t, 2J = 26.9 Hz), 131.1, 129.7, 129.0 (t, 3J = 5.3 Hz), 128.5 (t, 3J = 7.9 Hz), 128.4 (t, 3J = 3.4 Hz), 124.6 (t, 3J = 5.0 Hz), 122.1, 119.7 (t, 1J = 242.3 Hz), 52.1, 19.9, 19.4 

CDCl3, 282 MHz: –82.83 (s)

11

CDCl3, 300 MHz: 7.93 (t, 1H, J = 1.6 Hz). 7.80 (s, 1H), 7.64 (ddd, 1H, J = 7.7, 1.6, 1.2 Hz), 7.53 (dt, 1H, J = 7.7, 1.2 Hz), 7.35 (t, 1H, J = 7.7 Hz), 7.18 (s, 1H), 5.38 (m, 1H), 5.12 (m, 1H), 3.56 (s, 3H), 2.37 (s, 3H), 2.34 (s, 3H), 2.15 (m, 3H)

CDCl3, 75 MHz: 197.3, 166.7, 142.4, 141.9, 141.6, 139.2, 138.6, 137.5, 131.0, 129.9, 129.1, 128.6, 128.3, 126.8, 125.8, 113.5, 51.9, 21.7, 19.9, 19.6

 

12

CDCl3, 300 MHz: 7.55 (s, 1H), 7.42 (m, 1H), 7.38 (s, 1H), 7.36 (s, 1H), 7.26 (m, 1H), 7.24 (m, 1H), 5.29 (m, 1H), 5.03 (m, 1H), 3.54 (s, 3H), 2.25 (s, 3H), 2.23 (s, 3H), 2.06 (m, 3H)

CDCl3, 75 MHz: 168.6, 142.7, 141.2, 139.7, 138.8, 137.8 (t, 2J = 27.6 Hz), 132.5 (t, 2J = 27.3 Hz), 130.7, 128.7 (t, 3J = 3.4 Hz), 128.6 (t, 3J = 7.6 Hz), 128.0, 126.8 (t, 4J = 1.9 Hz), 125.0 (t, 3J = 5.2 Hz), 122.9 (t, 3J = 5.2 Hz), 120.6 (t, 1J = 241.6 Hz), 113.2, 52.0, 21.7, 19.9, 19.3

CDCl3, 282 MHz: – 82.49 (s)

13

CDCl3, 300 MHz: 7.77 (s, 1H), 7.67 (t, 1H, J = 1.6 Hz), 7.54 (dt, 1H, J = 7.5, 1.6 Hz), 7.42 (dt, 1H, J = 7.5, 1.6 Hz), 7.36 (t, 1H, J = 7.5 Hz), 7.20 (s, 1H), 3.70 (d, 2H, J = 6.9 Hz), 3.51 (s, 3H), 2.97 (sext., 1H, J = 6.9 Hz), 2.37 (s, 3H), 2.34 (s, 3H), 1.71 (br. s, 1H), 1.26 (d, 3H, J = 6.9 Hz)

CDCl3, 75 MHz: 197.3, 167.0, 144.4, 141.9, 139.0, 138.7, 137.8, 132.2, 130.9, 129.2, 128.7, 127.8 (2C), 127.1, 68.4, 51.9, 42.3, 19.9, 19.6, 17.5197.3, 167.0, 144.4, 141.9, 139.0, 138.7, 137.8, 132.2, 130.9, 129.2, 128.7, 127.8 (2C), 127.1, 68.4, 51.9, 42.3, 19.9, 19.6, 17.5

 

14

CDCl3, 300 MHz: 7.43 (s, 1H), 7.32 (s, 1H), 7.25 (s, 1H), 7.23 (s, 2H), 7.16–7.21 (m, 1H), 3.53 (d, 2H, J = 6.9 Hz), 3.46 (s, 3H), 2.83 (sext., 1H, J = 6.9 Hz), 2.24 (s, 3H), 2.21 (s, 3H), 2.14 (br. s, 1H), 1.14 (d, 3H, J = 6.9 Hz)

CDCl3, 75 MHz: 168.7, 143.9, 139.7, 138.8, 137.7 (t, 2J = 27.4 Hz), 132.4 (t, 2J = 27.3 Hz), 130.6, 128.8 (t, 4J = 1.7 Hz), 128.7 (t, 3J = 3.5 Hz), 128.3 (t, 3J = 7.7 Hz), 128.2, 125.1 (t, 3J = 5.1 Hz), 124.1 (t, 3J = 5.2 Hz), 120.4 (t, 1J = 241.3 Hz), 68.3, 52.0, 42.2, 19.8, 19.3, 17.3

CDCl3, 282 MHz: – 82.21 (s)

15

CDCl3, 300 MHz: 7.52 (m, 1H), 7.74 (m, 1H), 7.28 (m, 1H), 7.26 (m, 1H), 7.14–7.19 (m, 2H), 4.43 (s, 2 H), 2.21 (s, 3H), 2.19 (s, 3H), 1.82 (s, 1H)

CDCl3, 75 MHz: 139.5 (t, 4J = 1.5 Hz),139.5 (t, 2J = 28.8 Hz),136.2 (t, 3J = 2.1 Hz), 135.8, 133.3 (t, 4J = 1.8 Hz), 130.9, 130.4 (t, 2J = 26.2 Hz), 130.0, 129.1 (t, 3J = 5.2 Hz), 127.8 (t, 3J = 7.9 Hz), 124.7 (t, 3J = 5.2 Hz), 122.5, 120.8 (t, 1J = 241.8 Hz), 62.0 (t,4J = 3.4 Hz), 19.5 (2C)

CDCl3, 282 MHz: -83.28 (s)

16

CDCl3, 300 MHz: 7.53 (s, 1H), 7.45 (m, 1H), 7.29 (s, 1H), 7.25 (m, 1H), 7.21 (s, 2H), 5.29 (s, 1H), 5.05 (t, 1H, J = 1.4 Hz), 4.48 (s, 2H), 2.23 (s, 3H), 2.20 (s, 3H), 2.06 (dd, 3H, J = 1.4, 0.8 Hz)

CDCl3, 75 MHz: 142.5, 141.6, 139.3, 137.4 (t, 2J = 28.0 Hz), 136.3 (t, 4J = 2.1 Hz), 135.7, 131.3 (t,2J = 26.5 Hz), 131.1, 128.3, 128.0 (t, 3J = 7.8 Hz), 127.3 (t, 3J = 1.8 Hz), 125.1 (t, 3J = 5.2 Hz), 122.9 (t, 3J = 5.2 Hz), 121.7 (t, 1J = 241.5 Hz), 113.5, 62.2 (t, 4J = 3.2 Hz), 21.7, 19.5 (2C)

CDCl3, 282 MHz: – 82.87 (s)

17

(CDCl3, 500 MHz): 7.44 (s, 1H), 7.42 (s, 1H), 7.36 (s, 1H), 7.23–7.29 (m, 2H), 7.21 (m, 1H), 3.57 (s, 3H), 2.9 (sext., 1H, J = 6.9 Hz), 2.31 (s, 3H), 2.30 (s, 3H), 1.23 (d, 6H, J = 6.9 Hz)

(CDCl3, 125 MHz):168.7, 148.8, 139.6, 138.7, 137.7 (t, 2J = 27.3 Hz), 132.6 (t, 2J = 27.3 Hz), 130.7, 128.8 (t, 3J = 3.4 Hz), 128.6 (t, 3J = 7.6 Hz), 128.0, 127.8 (t, 4J = 1.8 Hz), 123.9 (t, 3J = 5.0 Hz), 123.6 (t, 3J = 5.2 Hz), 120.7 (t, 1J = 241.2 Hz), 52.0, 34.1, 23.9 (2C), 19.9, 19.4

(CDCl3, 470 MHz): – 81.94 (s)

18

CDCl3, 300 MHz: 7.25 (s, 1H), 7.23 (s, 1H), 7.16 (s, 1H), 7.14 (s, 1H), 7.12 (m, 1H), 7.05 (m, 1H), 4.39 (s, 2 H), 2.76 (sext., 1H, J = 6.9 Hz), 2.41 (br. s, 1H), 2.13 (s, 3H), 2.12 (s, 3H), 1.1 (d, 6H, J = 6.9 Hz)

CDCl3, 75 MHz: 149.1138.9, 137.3 (t, 2J = 27.8 Hz), 136.4, 135.2, 131.1 (t, 2J = 26.5 Hz), 130.5, 128.3, 128.0 (t, 4J = 1.7 Hz), 127.7 (t, 3J = 7.8 Hz), 123.9 (t, 3J = 5.0 Hz), 123.6 (t, 3J = 5.2 Hz),121.7 (t, 1J = 240.8 Hz), 61.6 (t, 4J = 3.2 Hz), 33.9, 23.7 (2C), 19.3 (2C)

CDCl3, 282 MHz: − 82.66 (s)

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