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ChemicalBook CAS DataBase List 2-bromo-5-(tert-butyl)-1,3-dimethylbenzene

2-bromo-5-(tert-butyl)-1,3-dimethylbenzene synthesis

4synthesis methods
-

Yield:5345-05-1 90%

Reaction Conditions:

with bromine;iron in chloroform at 0 - 20; for 3 h;Inert atmosphere;

Steps:

1.1 Synthesis of 2-Bromo-5-tert-butyl-1,3-dimethylbenzene (2)
In a 250 mL round-bottom flask equipped with a magnetic stir bar and an addition funnel were added5-tert-butyl-m-xylene (91.0 mL, 480 mmol) and iron powder (1.00 g, 1.36 mmol) to 75 mL of chloroform.The solution was cooled to 0 °C. A solution of bromine (27.5 mL, 525 mmol) in 25 mL of solution ofchloroform was added dropwise via the addition funnel. The reaction was stirred for 3 h at roomtemperature and then poured into a cold solution of dilute aqueous NaOH (~1 M). The mixture wasseparated, and the aqueous layer was washed several times with CH2Cl2. The combined organic layerswere dried with MgSO4, filtered, and concentrated to a clear oil, which became a white solid uponstanding. The crude solid was recrystallized from ethanol to give 105 g (437 mmol, 90% yield) of the titlecompound.

References:

Adachi, Yohei;Nakamoto, Masaaki;Shang, Rong;Yamamoto, Yohsuke;Yan, Chenting [Chemistry Letters,2020,vol. 49,# 5,p. 457 - 460] Location in patent:supporting information

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