Related Products of 51776-71-7, A common heterocyclic compound, 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, molecular formula is C7H5BrF2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: Under an argon atmosphere, degassed CCl4 (0.35 M) was addedto a round bottom flask containing the corresponding difluoromethyl arene (1.0 equiv.) and N-Bromosuccinimide (1.7 equiv.). The reaction mixture was irradiated by the light of a 120 W sun lamp (approx. 12 cm distance between lamp and reaction flask) for 1-30 days before being quenched with Na2S2O3 (sat. aq.) and extracted with CH2Cl2 (330 mL). The combined organic layers were washed with brine, dried over MgSO4 and the solvent was removed under reduced pressure. Purification by column chromatography afforded the desired bromodifluoromethyl arenes. 1-Bromo-4-(bromodifluoromethyl)benzene (3c). Following the general procedure B from 4-bromobenzaldehyde with a reaction time of 2 days. Purification by column chromatography (SiO2; pentane/Et2O 100:1) afforded 1-Bromo-4-(difluoromethyl)benzene as a colorless oil (1.05 g, 81%). 1H NMR (400 MHz,CDCl3, TMS): d = 7.62-7.58 (m, 2H), 7.41-7.36 (m, 2H), 6.61 (t, J(H,F) = 56.3 Hz, 1H). 13C NMR (100 MHz, CDCl3, TMS): d = 133.4 (t, J(C,F) = 22.8 Hz), 132.1, 127.4 (t, J(C,F) = 6.0 Hz), 125.3 (t, J(C,F) = 2.5 Hz),114.3 (t, J(C,F) = 239.2 Hz). 19F NMR (377 MHz, CDCl3): d =111.10(d, J(F,H) = 56.3 Hz). (EI) m/z (rel intens) 207.89 (M+, 81Br, 100),205.98 (M+, 79Br, 93), 127.23 (M+-Br, 49). From 1-Bromo-4-(difluoromethyl)benzene with a reaction time of 9 days. Purification by column chromatography (SiO2; pentane) afforded the title compound as a colorless oil (745 mg, 82%). 1H NMR (400 MHz,CDCl3, TMS): d = 7.62-7.58 (m, 2H), 7.50-7.46 (m, 2H). 13C NMR(100 MHz, CDCl3, TMS): d = 137.3 (t, J(C,F) = 24.2 Hz), 132.1, 126.1 (t, J(C,F) = 5.1 Hz), 126.0 (t, J(C,F) = 1.7 Hz), 117.8 (t, J(C,F) = 303.7 Hz). 19FNMR (377 MHz, CDCl3): d =44.05 (s). (EI) m/z (rel intens) 207.19(M+79Br-Br, 96), 205.17 (M+81Br-Br, 100), 126.23 (M+-Br2, 47).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Article; Bermejo Gome, Antonio; Gonzalez, Miguel A. Cortes; Luebcke, Marvin; Johansson, Magnus J.; Schou, Magnus; Szabo, Kalman J.; Journal of Fluorine Chemistry; vol. 194; (2017); p. 51 – 57;,
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