ChemicalBook CAS DataBase List 4-BroMo-2,5-diMethylbenzaldehyde

4-BroMo-2,5-diMethylbenzaldehyde synthesis

7synthesis methods

Product Name:4-BroMo-2,5-diMethylbenzaldehyde
CAS Number:88111-74-4
Molecular formula:C9H9BrO
Molecular Weight:213.07

2591-86-8 Synthesis

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Yield:-

Reaction Conditions:

Stage #1: 2,5-dibromo-p-xylenewith n-butyllithium in tetrahydrofuran;hexane at -78; for 2 h;
Stage #2: N-Formylpiperidine in tetrahydrofuran;hexane at -78 - 20; for 2 h;

Steps:

4-bromo-2,5-dimethylbenzaldehyde (6)

To a solution of 1,4-dibromo-2,5-dimethylbenzene (7.83 g, 30 mmol) in dry THF (150 mL), BuLi solution (2.5 M in n-hexane, 14.4 mL, 36 mmol) was added slowly at -78 °C. After being stirred for 2 h, 1-formylpiperidine (10 mL) was added in dropwise. The reaction was warmed to room temperature, stirred for 2 h, and quenched with HCl (2 M). The residue was extracted with ethyl acetate, washed with brine, dried over MgSO4, and evaporated under reduced pressure, giving the crude compound which was purified by flash chromatography with hexane/ethyl acetate (10:1) as eluent to afford the title compound as a white solid.

References:

Sun, Qi;Pan, Yanxiong;Wang, Xiaoliang;Li, Hui;Farmakes, Jasmin;Aguila, Briana;Yang, Zhongyu;Ma, Shengqian [Chem,2019,vol. 5,# 12,p. 3184 - 3195] Location in patent:supporting information