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Citation: Heng Zhang, Zhirong Xing, Dong Liu, Zhibin Zhou, Wenfang Feng. Improvement on Synthesis of Grignard Reagent[J]. University Chemistry, ;2023, 38(2): 177-184. doi: 10.3866/PKU.DXHX202205011 shu

Improvement on Synthesis of Grignard Reagent

School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, China

Corresponding author: Wenfang Feng, fengwenfang@mail.hust.edu.cn
Received Date: 6 May 2022

In this work, the synthesis of Grignard reagent is improved by replacing molecular iodine with diisobutylaluminum hydride (DIBAH). Systematic investigations on the influence of DIBAH initiation on the safety of the reaction system and the chemical structure of haloalkanes are performed. It has been demonstrated that the addition of 2 mol% DIBAH (vs. the molar content of haloalkanes) allows the reaction to take place under mild condition (20 °C), yielding phenyl magnesium bromide and n-butyl magnesium bromide with high efficiency. With the improved safety on modified Grignard reactions, the students could get a deeper understanding on the importance of safety in chemical reactions. In particular, the present work could also help students to pay attention to safety of organic experiments and the dilemmas encountered by practical applications, and better cope with the gap between fundamental research and industrial applications.
- Experimental safety,
- Grignard reagent,
- Triphenylmethanol,
- 2-Methyl-2-hexanol
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
7. [7]
  Peltzer, R. M.; Gauss, J.; Eisenstein, O.; Cascella, M. J. Am. Chem. Soc. 2020, 142 (6), 2984.
8. [8]
  Rachon, J.; Walborsky, H. M. Tetrahedron Lett. 1989, 30 (52), 7345.
9. [9]
10. [10]
11. [11]
  Tilstam, U.; Weinmann, H. Org. Process Res. Dev. 2002, 6 (6), 906.
12. [12]
13. [13]
14. [14]
15. [15]
16. [16]
1. [1]
  Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
2. [2]
  Jian Jin , Jing Cheng , Xueping Yang . Integration Practice of Organic Chemistry Experiment and Safety Education: Taking the Synthesis of Triphenylmethanol as an Example. University Chemistry, 2024, 39(3): 345-350. doi: 10.3866/PKU.DXHX202309010
3. [3]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
4. [4]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
5. [5]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
6. [6]
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7. [7]
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8. [8]
  Kangmin Wang , Liqiu Wan , Jingyu Wang , Chunlin Zhou , Ke Yang , Liang Zhou , Bijin Li . Multifunctional 2-(2′-hydroxyphenyl)benzoxazoles: Ready synthesis, mechanochromism, fluorescence imaging, and OLEDs. Chinese Chemical Letters, 2024, 35(10): 109554-. doi: 10.1016/j.cclet.2024.109554
9. [9]
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10. [10]
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11. [11]
  Jin Yan , Chengxia Tong , Yajie Li , Yue Gu , Xuejian Qu , Shigang Wei , Wanchun Zhu , Yupeng Guo . Construction of a “Dual Support, Triple Integration” Chemical Safety Practical Education System. University Chemistry, 2024, 39(7): 69-75. doi: 10.12461/PKU.DXHX202405008
12. [12]
  Yue Li , Minghao Fan , Conghui Wang , Yanxun Li , Xiang Yu , Jun Ding , Lei Yan , Lele Qiu , Yongcai Zhang , Longlu Wang . 3D layer-by-layer amorphous MoS_x assembled from [Mo₃S₁₃]^2- clusters for efficient removal of tetracycline: Synergy of adsorption and photo-assisted PMS activation. Chinese Chemical Letters, 2024, 35(9): 109764-. doi: 10.1016/j.cclet.2024.109764
13. [13]
  Chuanli Qin , Naiying Fan , Yan Wang , Bin Wang , Guo Zhang , Bing Zheng , Yichun Qu , Zhiyao Sun , Guanghui An . Teaching Design and Exploration of Ideological and Political Education in Chemical Experiment Safety Courses: a Case Study of the “Chemical Experiment Safety” Course at Heilongjiang University. University Chemistry, 2024, 39(2): 234-241. doi: 10.3866/PKU.DXHX202308008
14. [14]
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15. [15]
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16. [16]
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17. [17]
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18. [18]
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19. [19]
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20. [20]
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