[Br:1]C1C=C(F)C(C#N)=C(F)C=1.[CH2:12]([OH:16])[CH2:13][CH2:14][OH:15].O.[C:18]1([CH3:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:20]1[CH:19]=[C:18]([CH:24]2[O:16][CH2:12][CH2:13][CH2:14][O:15]2)[CH:23]=[CH:22][CH:21]=1A solution of 3-bromobenzaldehyde (1, 18.5 g, 100 mmol), propane-1,3-diol (9.1 g, 120 mmol) and p-toluenesufonic acid monohydrate (0.1 g, 0.5 mmol) in toluene (200 mL) was refluxed with azeotropical removal of water using a Dean-Stark water separator for 15.5 h. The reaction mixture was cooled to room temperature, washed with 5% potassium carbonate solution (100 mL) and water (2×100 mL), dried over sodium sulfate and filtered. The filtrate was concentrated to afford the title compound (24.8 g, 100%): 1H NMR (500 MHz, CDCl3) δ 7.66 (t, J=1.8 Hz, 1H), 7.46 (ddd, J=7.9, 2.0, 1.1 Hz, 1H), 7.40 (br d, J=7.9 Hz, 1H), 7.23 (t, J=7.9 Hz, 1H), 5.46 (s, 1H), 4.28-4.25 (m, 2H), 4.00-3.95 (m, 2H), 2.26-2.17 (m, 1H), 1.47-1.43 (m, 1H); ESI MS m/z 243, 245 [M+H]+.
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