HBr催化α-溴代甲基酮类化合物的全脱溴反应研究

doi:10.6023/cjoc202010006

有机化学 ›› 2021, Vol. 41 ›› Issue (5): 2121-2126.DOI: 10.6023/cjoc202010006 上一篇下一篇

研究简报

HBr催化α-溴代甲基酮类化合物的全脱溴反应研究

郑梦霞^a, 曾竟^a, 买里克扎提•买合木提^b^,^*(), 阿布都热西提•阿布力克木^a^,^*()

a 新疆师范大学化学系乌鲁木齐 830054
b 新疆大学化工学院乌鲁木齐 830046

收稿日期:2020-10-06 修回日期:2020-12-14 发布日期:2021-02-22
通讯作者: 买里克扎提?买合木提, 阿布都热西提?阿布力克木
基金资助:
新疆维吾尔自治区2017年自治区“天山青年计划”(2017Q026)

Study on the Debromination of α-Bromomethyl Ketones Catalyzed by HBr

Mengxia Zheng^a, Jing Zeng^a, Mailikezhati Meihemuti^b^,^*(), Abudu Rexit Abulikemu^a^,^*()

a Department of Chemistry, Xinjiang Normal University, Urumqi 830054
b School of Chemical Engineering, Xinjiang University, Urumqi 830046

Received:2020-10-06 Revised:2020-12-14 Published:2021-02-22
Contact: Mailikezhati Meihemuti, Abudu Rexit Abulikemu
About author:
* Corresponding authors. E-mail: aarexit@xjnu.edu.cn;
E-mail: amelikezat@xju.edu.cn
Supported by:
Xinjiang Uygur Autonomous Region 2017 Tianshan Youth Program(2017Q026)

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摘要/Abstract

报道了HBr催化下以水为氢源的α-溴代甲基酮类化合物的脱溴化反应. 以α-溴代甲基酮类化合物为原料, 四氢呋喃为溶剂, α-溴代甲基酮与质量分数5%的氢溴酸的物质的量比为1.0:0.2时, 在180 ℃下反应5~14 h, 分离产率高达94% [高效液相(HPLC)产率96%]的脱溴产物. 该方法无金属催化剂参与, 催化剂价格低廉, 所有产物均经¹H NMR和¹³C NMR结构确证.

关键词: α-溴代甲基酮类化合物, HBr, 脱溴

The debromination reaction of α-bromomethylketone compounds was achieved by using water as the hydrogen source under the catalysis of HBr. Using α-bromomethylketones as raw materials, tetrahydrofuran as solvent, when the molar ratio of α-bromomethylketone to 5% mass fraction hydrobromic acid was 1.0:0.2, the debrominated product could be obtained with a isolated yield of 94% [high performance liquid chromatography (HPLC) yield 96%] by reacting at 180 ℃ for 5~14 h. All products were confirmed by¹H NMR and ¹³C NMR spectra.

Key words: α-bromomethylketone, HBr, debromination

引用此文

郑梦霞, 曾竟, 买里克扎提•买合木提, 阿布都热西提•阿布力克木. HBr催化α-溴代甲基酮类化合物的全脱溴反应研究[J]. 有机化学, 2021, 41(5): 2121-2126.

Mengxia Zheng, Jing Zeng, Mailikezhati Meihemuti, Abudu Rexit Abulikemu. Study on the Debromination of α-Bromomethyl Ketones Catalyzed by HBr[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2121-2126.

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HBr催化α-溴代甲基酮类化合物的全脱溴反应研究

Study on the Debromination of α-Bromomethyl Ketones Catalyzed by HBr

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Entry	Mass fraction of HBr/%	HBr/equiv.	Solvent	V(solvent)/mL	T/℃	Time/h	Yield^b/%
1	0	0	THF	1	150	33	37
2	0	0	THF	1	180	12	46
3^c	5	0.2	THF	1	180	12	45
4	10	0.1	THF	1	150	33	67
5	20	0.1	THF	1	150	33	66
6	5	0.1	THF	1	150	35	71
7	5	0.2	THF	1	150	35	79
8	5	0.3	THF	1	150	35	74
9	5	0.2	2-MeTHF	1	150	33	71
10	5	0.2	DMSO	1	150	33	Trace
11	5	0.2	CH₃OH	1	150	48	5
12	5	0.2	1,4-Dioxane	1	150	33	61
13	5	0.2	THF	0.5	180	7	63
14	5	0.2	THF	1	180	7	88 (96^d)
15	5	0.2	THF	2	180	7	87
16	5	0.2	THF	1	130	82	63

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