5-BROMOTHIOPHENE-2-BORONIC ACID

white to light yellow crystal powder

General procedure: Added to a 250-mL dried Schlenk flask were 2, 4-dibromo-1-isopropoxybenzene 4 (0.1 g or 0.340 mmol), tetrakis(triphenylphosphine)palladium(0) (5 mol%) along with a magnetic stirrer, and 1, 4-dioxane (4 mL). The mixture was enclosed with a Teflon septum and stirred at about room temperature for 30 min. Arylboronic acid (2.5 equiv.), potassium phosphate (2 equiv.), and 1 mL of distilled water were also added to the above mixture under an inert argon atmosphere for 12 h at approximately 90 C. After completion of the reaction, the resulting crude mixture was cooled to about 25 C and diluted with C2H5COOCH3, and the organic layer was separated. The impure product was purified using column chromatography [42-45].1. Synthetic routeWherein, the condition (f) is PdCl2(dppf), Pd(OAc)2, K3PO4, toluene, 100 to 105 C, 16 to 24 hours.2, the synthesis step(1) Weigh 200mg (0.38mmol, 0.38mmol, 0.41mmol) after purification of the compound 1, 2, 3 of Example 4, 4 times the mass of K3PO4 (1.52 mmol, 1.52 mmol, 1.64 mmol) was added. And adding 0.1 times the mass of PdCl2(dppf) (0.038 mmol) and 0.02 times the mass of Pd(OAc)2 (0.0076 mmol), Next, add 2 times the mass of boric acid (mono- or poly-substituted aryl boronic acid, Including non-heterocyclic aryl boronic acid or heterocyclic aryl boronic acid) (0.76 mmol), Add 30mL of toluene solvent, under the protection of nitrogen conditions, magnetic stirring, the reaction was carried out in an oil bath at 100 C for 16 h or more; the reaction end point was detected by TLC [developing agent: V (petroleum ether) / V (ethyl acetate) = 50/1];(2) After the reaction is over, add 50 mL of deionized water. Extracted directly with ethyl acetate three times, dried over anhydrous MgSO4. Then, it was filtered and concentrated to give a crude product, which was purified by silica gel column chromatography (eluent: V( petroleum ether)/V(ethyl acetate) = 100/1] the target compound bifenthrin derivative (Compound 4-18) is obtained as a colorless oily liquid. It was characterized by 1H NMR, 13C NMR, HRMS, etc. for molecular structure analysis.General procedure: The catalyst Pd(PPh3)4 (5 mol%) was added in the Schiff bases (0.712 mmol, 1 eq), under an inert nitrogen atmosphere. The reaction mixture was stirred for 30 min after addition of a 1, 4-dioxane solvent (8 mL). Then, aryl/het-aryl boronic acids (0.783 mmol, 1.1 eq), K3PO4 (1.43 mmol, 2 eq) and H2O (2 mL) were added [26, 27] and stirring of mixture was done for 20-25 h at 90 C. The mixture was diluted with ethyl acetate at room temperature. The separated organic layer was dried with magnesium sulphate (MgSO4) and the solvent was removed under a vacuum. The crude product was purified by column chromatography using ethyl-acetate and n-hexane. For characterization of synthesized products, different spectroscopic techniques were used.General procedure: The catalyst Pd(PPh3)4 (5 mol%) was added in the Schiff bases (0.712 mmol, 1 eq), under an inert nitrogen atmosphere. The reaction mixture was stirred for 30 min after addition of a 1, 4-dioxane solvent (8 mL). Then, aryl/het-aryl boronic acids (0.783 mmol, 1.1 eq), K3PO4 (1.43 mmol, 2 eq) and H2O (2 mL) were added [26, 27] and stirring of mixture was done for 20-25 h at 90 C. The mixture was diluted with ethyl acetate at room temperature. The separated organic layer was dried with magnesium sulphate (MgSO4) and the solvent was removed under a vacuum. The crude product was purified by column chromatography using ethyl-acetate and n-hexane. For characterization of synthesized products, different spectroscopic techniques were used.General procedure: The catalyst Pd(PPh3)4 (5 mol%) was added in the Schiff bases (0.712 mmol, 1 eq), under an inert nitrogen atmosphere. The reaction mixture was stirred for 30 min after addition of a 1, 4-dioxane solvent (8 mL). Then, aryl/het-aryl boronic acids (0.783 mmol, 1.1 eq), K3PO4 (1.43 mmol, 2 eq) and H2O (2 mL) were added [26, 27] and stirring of mixture was done for 20-25 h at 90 C. The mixture was diluted with ethyl acetate at room temperature. The separated organic layer was dried with magnesium sulphate (MgSO4) and the solvent was removed under a vacuum. The crude product was purified by column chromatography using ethyl-acetate and n-hexane. For characterization of synthesized products, different spectroscopic techniques were used.

Molecular Weight:206.86
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:205.92084
Monoisotopic Mass:205.92084
Topological Polar Surface Area:68.7
Heavy Atom Count:9
Complexity:103
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes