Electric Literature of 1073-06-9, A common heterocyclic compound, 1073-06-9, name is 1-Bromo-3-fluorobenzene, molecular formula is C6H4BrF, 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: An oven dried round-bottom flask was charged with magnesium (1.2 equiv.), applied high vacuum three times and back filled with nitrogen. Then a small piece iodine (I2) and solvent dry THF 5 mL was added under N2 atmosphere. Solution of aryl bromide (1.0 equiv. 3 mmol) in 5 mL of dry THF was dropped slowly to the round bottom flask and stirred at room temperature for 30 min under N2 atmosphere. After the formation of Grignard reagent, the reaction mixture was cooled to 0 C and then corresponding aldehyde 1.5 equiv. was added dropwise. The reaction mixture was stirred for 1-2 h. Progress of the reaction was monitored by TLC. After consumption of reactants, the reaction mixture was quenched with sat. NH4Cl solution and extracted with ethyl acetate (3 * 20 mL). The combined organic layer was washed with sat. NaCl solution and dried over anhydrous Na2SO4. The organic layer was concentrated under vacuum, and the crude mixture was purified by silica gel column chromatography (hexanes/ethyl acetate) to afford pure secondary benzyl alcohols 1.
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; Muneeswara, Madithedu; Sundaravelu, Nallappan; Sekar, Govindasamy; Tetrahedron; vol. 75; 25; (2019); p. 3479 – 3484;,
Bromide – Wikipedia,
bromide – Wiktionary