ChemicalBook CAS DataBase List 4-Bromobenzyl alcohol

4-Bromobenzyl alcohol synthesis

12synthesis methods

Product Name:4-Bromobenzyl alcohol
CAS Number:873-75-6
Molecular formula:C7H7BrO
Molecular Weight:187.03

586-76-5
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$10.00/1g

873-75-6
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$6.00/5g

Yield:873-75-6 93%

Reaction Conditions:

Stage #1:4-Bromobenzoic acid with 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 20; for 12 h;Inert atmosphere;
Stage #2: with silica gel in methanol at 50; for 3 h;

Steps:

6 Embodiment 6: [...] borane and 4 - bromobenzoic acid 4:1 molar ratio
In the inert gas N2 atmosphere, after dehydration and deoxidation treatment to the reaction bottle after adding 4 - bromobenzoic acid (100 mg, 0.5 mmol), for adding liquid-[...] borane (289 μl, 2 mmol), reacting at room temperature 12 hours, the reaction out of the glove box, in order to have three methoxybenzene (83.67 mg, 0.5 mmol) as the internal standard, CDCl3 for dissolving, stirring 10 minutes, sampling, with nuclear magnetic resonance. Calculated 1 H and the yield is 95%. The product of nuclear magnetic data: The residue is added to the sample in 1 g silica gel, in order to 3 ml methanol as a solvent, 50 °C lower reaction 3 h, the borate further hydrolysis alcohol, after the reaction, extracted with ethyl acetate three times, the combined organic layer, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, through the silica gel (100 - 200 mesh) column chromatography purification, ethyl acetate/hexane (1:5) mixture as the eluent, to obtain the pure primary alcohol, separation and the yield is 93%.

References:

Soochow University (Suzhou);Xue Mingqiang;Xu Xiaojuan;Yan Dandan;Kang Zihan;Zhu Zhangye;Shen Qi CN109574808, 2019, A Location in patent:Paragraph 0020

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