2-(3-Chloro-5-fluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane synthesis

Yield:1422022-15-8 74.45 %

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium acetate in 1,4-dioxane at 80;Inert atmosphere;

Steps:

12.1 Synthesis of Compound 12-1

At room temperature, compound 5-bromo-1-chloro-3-fluoro-2-methoxybenzene (8.7 g), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)-1,3,2-dioxaborane (13.84 g) and KOAc (10.68 g) were dissolved in dioxane (87 mL). In the nitrogen protection atmosphere, Pd(dppf)Cl₂ (2.96 g) was added into it, and the reaction mixture was moved to 80° C. for reaction for 2 h. The reaction solution was diluted with water, extracted with EA three times, the organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The concentrate was purified by silica gel column chromatography (PE:DCM=10:1) to obtain the target product (7.75 g, 74.45% yield), compound 12-1, as a colorless oil

References:

US2023/62486,2023,A1 Location in patent:Paragraph 0148; 0149