1-ethenyl-2,4-difluorobenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared according to the method of preparation of Intermediate 1, Step 2, using 2-{2-[(4-bromophenyl)sulfonyl]phenyl}-1,3,4-oxadiazole (Step 1) in place of 3-[(4-bromophenyl)sulfonyl]propanenitrile and 2,4-difluorostyrene in place of 4-fluorostyrene. δH (500 MHz, d6 DMSO): 9.45 (1H, s), 8.35 (1H, d, J 7.8), 7.97-7.85 (8H, m), 7.47-7.31 (3H, m), 7.17 (1H, t, J 8.6). m/z (ES+) 425 [MH+].

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4.2 g of 2,4-difluorostyrene and 4.55 g of ethyl 2-chloro-2-hydroximinoacetate are introduced into 350 ml of ether, and the mixture is cooled to 0° C. 3.03 g of triethylamine are added dropwise to this mixture at 0° C. The mixture is stirred for 3 hours at room temperature, 50 ml of water are then added, and the mixture is extracted using ether. After drying over MgSO4, the ether is distilled off, and the residue is purified over a silica column (eluent: n-heptane:ethyl acetate=8:2). This gave 6.68 g (86% of theory) of product of refractive index [n]D20 =1.5019. the mixture is extracted After drying over MgSO4 the ether is distilled off the residue is purified over a silica column (eluent: n-heptane:ethyl acetate=8:2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared according to the method of preparation of Intermediate 1, Step 2, using 2-{2-[(4-bromophenyl)sulfonyl]phenyl}-1,3,4-oxadiazole (Step 1) in place of 3-[(4-bromophenyl)sulfonyl]propanenitrile and 2,4-difluorostyrene in place of 4-fluorostyrene. δH (500 MHz, d6 DMSO): 9.45 (1H, s), 8.35 (1H, d, J 7.8), 7.97–7.85 (8H, m), 7.47–7.31 (3H, m), 7.17 (1H, t, J 8.6). m/z (ES+) 425 [MH+].