Extracurricular laboratory: Synthetic route of 14804-31-0

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.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Step b: To a degassed (argon) solution of 3b (10.0 g, 49.7 [MMOL)] in DMF (310 mL) was added bis (pinacolato) diborane (13.9 g, 54.7 [MMOL), KOAC] (14.2 g, 149 [MMOL)] and [PDCL2DPPF] (1: 1 complex with [CH2CI2,] 4.87 g, 5.96 [MMOL).] The reaction mixture was heated to 80 C for 24 h then was cooled to 25 [C.] 4-Bromobenzeneacetic acid (21.4 g, 99.5 [MMOL),] aqueous 2 M [NA2CO3 SOLUTION] (124 mL, 248 [MMOL)] and additional [PDCI2DPPF] (1: 1 complex with [CH2CI2,] 4.87 g, 5.96 [MMOL)] were added to the mixture. The reaction mixture was heated to [80 C] for 12 h. The cooled mixture was acidified with aqueous 4 N HCI solution and extracted with EtOAc (3 x). The combined organic layers were successively washed with water (2 x) and brine, dried [(MGS04),] filtered and concentrated under reduced pressure. The crude resulting acid was dissolved in [ET2O] and was treated with excess ethereal [CH2N2] solution (ca. 0.6 M). The mixture was concentrated under reduced pressure. The residue was purified by flash chromatography (hexane/EtOAc, 19/1) to give 3c (4.25 g, 32% yield) as a pale yellow solid.

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:
Patent; BOEHRINGER INGELHEIM (CANADA) LTD.; WO2004/26875; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem