Sulfuric Acid → HCID 67458641, compound

In a nitrogen stream, a solution of 1-bromo-3-(4-ethylbenzyl)benzene (2.19 g, 7.96 mmol) in THF (20 mL) was cooled to −78° C., and an n-butyllithium hexane solution (2.44 M, 3.42 mL) was added dropwise thereto and the mixture solution was stirred at the same temperature for 20 minutes. After addition of trimethyl borate (2.68 mL, 23.87 mmol), the reaction mixture was stirred at the temperature for five minutes and at room temperature for 12.5 hours. After cooling the reaction mixture in an ice bath, concentrated sulfuric acid (10 mL) was added dropwise thereto and the mixture solution was stirred at the same temperature for one hour. The mixture was extracted with ether and the organic layer was washed with water and then dried over sodium sulfate. To a white solid obtained by distilling the solvent under reduced pressure was added hexane-ethyl acetate (10:1)(5 mL), the mixture was filterated and then the obtained solid was washed with hexane-ethyl acetate (10:1). The obtained white powder was dried under reduced pressure to obtain the title compound (604.2 mg, 32%).

1. stirringthe reaction mixture was stirred at the temperature for five minutes and at room temperature for 12.5 hours
2. temperatureAfter cooling the reaction mixture in an ice bath
3. stirringthe mixture solution was stirred at the same temperature for one hour
4. extractionThe mixture was extracted with ether
5. washthe organic layer was washed with water
6. dry with materialdried over sodium sulfate
7. customTo a white solid obtained
8. distillationby distilling the solvent under reduced pressure
9. additionwas added hexane-ethyl acetate (10:1)(5 mL)
10. washthe obtained solid was washed with hexane-ethyl acetate (10:1)
11. customThe obtained white powder was dried under reduced pressure

ORD record

ord-fafd632d96184078bdc430c82934f489

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08048897B2