These common heterocyclic compound, 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, 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. Recommanded Product: 142808-15-9
To a reaction vessel under a nitrogen atmosphere, 4-bromo-2-fluoro-1-(trifluoromethyl)benzene (2.28 g) and diethyl ether (70 ml) were added, and cooling was carried out to-70C. Thereto, a n-butyllithium (1.57 M) n-hexane solution (7.10 ml) was added dropwise in a temperature range of -70C to -65C, and stirring was carried out for another 1 hour. Subsequently, a diethyl ether (10 ml) solution of compound (T-9) (2.68 g) was added dropwise in a temperature range of -70C to -65C, and stirring was carried out for 4 hours while returning to room temperature. The resultant reaction mixture was poured into ice water (100 ml), and mixing was carried out. Toluene (100 ml) was added to separate layers into an organic layer and an aqueous layer, and an extraction operation was performed. The resultant organic layer was sequentially washed with a 1 N hydrochloric acid solution, a saturated aqueous solution of sodium hydrogencarbonate and water, and drying over anhydrous magnesium sulfate was carried out. The resultant solution was concentrated under reduced pressure, and a residue was purified by fractionation by means of column chromatography (silica gel; heptane), and further purified by recrystallization from a heptane/Solmix A-11 mixed solvent, and thus (E)-1-(1,2-difluoro-2-[3-fluoro-4-(trifluoromethyl)phenyl]vinyl)-2 -fluoro-4-(4-propylcyclohexyl)benzene (1-1-25) (2.24 g) was obtained. The yield based on compound (T-9) was 57%. Chemical shifts according to 1H-NMR analysis were as described below, and the compound obtained could be identified to be (E)-1-(1,2-difluoro-2-[3-fluoro-4-(trifluoromethyl)phenyl]vinyl)-2 -fluoro-4-(4-propylcyclohexyl)benzene. Chemical shifts delta (ppm; CDCl3); 7.72 – 7.57 (m, 3H), 7.46 (dd, J = 7.65 Hz, J = 7.65 Hz, 1H), 7.10 (d, J = 8.05 Hz, 1H), 7.04 (d, J = 11.7 Hz, 1H), 2.52 (tt, J = 9.15 Hz, J = 3.15 Hz, 1H), 1.96 – 1.85 (m, 4H), 1.50 – 1.38 (m, 2H), 1.38 – 1.26 (m, 3H), 1.26 – 1.19 (m, 2H), 1.12 – 1. 01 (m, 2H), 0.91 (t, J = 7.30 Hz, 3H). A phase transition temperature of compound (1-1-25) obtained was as described below. Phase transition temperature: C 104 N 125 I.
The synthetic route of 4-Bromo-2-fluorobenzotrifluoride has been constantly updated, and we look forward to future research findings.
Reference:
Patent; JNC Corporation; JNC Petrochemical Corporation; EP2522649; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary