Introduction of a new synthetic route about 3-Bromobicyclo[4.2.0]octa-1,3,5-triene

According to the analysis of related databases, 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, the application of this compound in the production field has become more and more popular.

1073-39-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1073-39-8 as follows.

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (569 mg, 3.1 1 mmol, 1.00 equiv) in THF (12 mL) was added n-BuLi (2.5M in hexane, 1.30 mL, 1.05 equiv) dropwise at -78C, and the mixture was stirred at -78C for 30 min. 4-(Benzyloxy)-5-bromo-2-methoxybenzaldehyde (1 g, 3.1 1 mmol, 1.00 equiv) in THF (3 mL) was then added to the solution. The reaction mixture was stirred at -78C for 2 h. NH4CI/H20 was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2S04, then concentrated and purified by chromatography on silica gel (5:1 PE/EA) to yield 1 (4-(benzyloxy)-5-bromo-2-methoxyphenyl)(1,2- dihydrocyclobutabenzen-4-yl)methanol as a light yellow oil. MS (ES) m/z: 409.0 [M-OH]+

According to the analysis of related databases, 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary