Halogenation of Aromatic Compounds by N-chloro-, N-bromo-, and N-iodosuccinimide

Abstract

An efficient and mild method for the halogenation of aromatic compounds using N-chloro-, N-bromo-, and N-iodosuccinimide in the presence of NH4NO3 or FeCl3 in acetonitrile was developed.

A Versatile and Efficient Ligand for Copper‐Catalyzed Formation of CN, CO, and PC Bonds: Pyrrolidine‐2‐Phosphonic Acid Phenyl Monoester

“…2-Nitrophenyl phenyl ether (5 f): [44] White solid, yield 93 % (400 mg). [46] Colorless oil, yield 97 % (481 mg). + m/z calcd for C 12 H 9 BrO: 247.9837; found: 247.9831.…”

“…58-60 8C (lit. [46] 2-(4-Methoxyphenoxy)pyridine (5 m): [50] Colorless oil, yield 96 % (386 mg). General procedure for the preparation of compounds 8 a-j: Aryl halide (2 mmol), phosphonate (3 mmol), and PPAPM hydrochloride (104 mg, 0.4 mmol) were added to a flask with Cs 2 CO 3 (1432 mg, 4.4 mmol) and toluene (3 mL), the mixture was stirred for 30 min at room temperature under nitrogen atmosphere, and CuI (76.4 mg, 0.4 mmol) was added to the flask.…”

Electrophilic Cyclizations of 2‐Fluoroalk‐3‐yn‐1‐ones: Room‐Temperature Synthesis of Diversely 2,5‐Disubstituted 3,4‐Fluorohalofurans

“…According to literature reports on the electrophilic activity of halosuccinimides, we examined the influence of p-toluenesulfonic acid monohydrate [26] and, in a separate experiment, ammonium chloride. [27] In the presence of TsOH·H 2 O (20 mol-%), the halocyclization reaction was significantly accelerated. After 30 min, 6 h, and 16 h the yields of 3-fluoro-4-iodofuran 3a were 44 %, 63 %, and 40 %, respectively (Entries 6-8).…”

Halogenation of Tröger’s base analogues

“…The first set of reactions that were investigated involved the reaction of 1 and 2 with NBS in the presence of ammonium nitrate 33 as outlined in Scheme 1, with the results detailed in Table 1.…”

“…[25][26][27][28] As part of a preliminary study aimed at alternate ways of accessing functionalised Tröger's base analogues, a methodology to brominate and chlorinate four Tröger's base compounds, as racemic mixtures, (Figure 1) was investigated. Numerous methods to halogenate aromatic compounds exist, [29][30][31][32][33][34] however, in terms of ease of handling and health issues, N-halosuccinimides are excellent reagents, especially if benzylic halogenation is suppressed.…”