128-08-5Relevant articles and documents
TIN(IV) MEDIATED SYNTHESIS OF N-HALO COMPOUNDS
Soundararajan, R.,Krishnamurthy, S.,Srinivasan, Vilanoor S.,Balasubramanian, T.R.
, p. 295 - 298 (1983)
Some representative N-halo compounds like N-bromosuccinimide, N-iodosuccinimide, N-bromophthalimide, N-iodophthalimide, N-iodobenzimidazole and N-iodobenzotriazole have been synthesised in good yields under neutral and mild conditions via an intermediate formed from the parent NH species and bis(tri-n-butyltin) oxide.The tin oxide is recovered as recyclable tri-n-butyltin halide.
Organic Synthesis Using Sodium Bromate. II. A Facile Synthesis of N-Bromo Imides and Amides Using Sodium Bromate and Hydrobromic Acid (or Sodium Bromide) in the Presence of Sulfuric Acid
Fujisaki, Shizuo,Hamura, Satoshi,Eguchi, Hisao,Nishida, Akiko
, p. 2426 - 2428 (1993)
The reaction of imides and amides in water (or aqueous acetic acid) with sodium bromate and hydrobromic acid (or sodium bromide) in the presence of sulfuric acid under mild conditions gave the corresponding N-bromides in high yields.
A Practical Synthesis of N-Bromo Imides by Use of Sodium Bromite
Kajigaeshi, Shoji,Nakagawa, Takashi,Fujisaki, Shizuo,Nishida, Akiko
, p. 769 - 770 (1985)
N-Bromo imides can be readily prepared under mild conditions by a reaction of imides with sodium bromite in the presence of hydrobromic acid in fairly good yields.The scope and limitation are also presented.
Thiourea-Mediated Halogenation of Alcohols
Mohite, Amar R.,Phatake, Ravindra S.,Dubey, Pooja,Agbaria, Mohamed,Shames, Alexander I.,Lemcoff, N. Gabriel,Reany, Ofer
, p. 12901 - 12911 (2020/11/26)
The halogenation of alcohols under mild conditions expedited by the presence of substoichiometric amounts of thiourea additives is presented. The amount of thiourea added dictates the pathway of the reaction, which may diverge from the desired halogenation reaction toward oxidation of the alcohol, in the absence of thiourea, or toward starting material recovery when excess thiourea is used. Both bromination and chlorination were highly efficient for primary, secondary, tertiary, and benzyl alcohols and tolerate a broad range of functional groups. Detailed electron paramagnetic resonance (EPR) studies, isotopic labeling, and other control experiments suggest a radical-based mechanism. The fact that the reaction is carried out at ambient conditions, uses ubiquitous and inexpensive reagents, boasts a wide scope, and can be made highly atom economic, makes this new methodology a very appealing option for this archetypical organic reaction.
Preparation method of 2-amino-5-bromopyridine
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Paragraph 0018; 0020; 0022, (2018/04/01)
The invention discloses a preparation method of 2-amino-5-bromopyridine. The preparation method is characterized in that 2-aminopyridine is used as the raw material, and two different bromination agents, namely bromine and N-bromo-succinimide (NBS), are sequentially added; the reaction temperature is strictly controlled, and thus 2-amino-5-bromopyridine can be quickly prepared with high yield andhigh purity; and the preparation method is applicable to industrial production. Additionally, a high-purity by-product, namely succinimide, is separated out in the preparation process and is brominated into high-purity NBS through potassium bromide, potassium bromate and sulfuric acid; and the NBS is applied to the synthesizing of 2-amino-5-bromopyridine in the method and has the same effect as the commercial NBS. According to the method, the quantity of used NBS is decreased, the raw material conversion rate is increased, and the bromination agents are recycled, so that the cost is greatly decreased; the main byproduct is only inorganic salt potassium sulfate; and the synthesizing method is green and environmentally friendly.