Application and preparation method of 2-bromo-5-chloroaniline_Kain Industrial Additive

Background and overview^[1]

2-Bromo-5-chloroaniline is an organic chemical substance, which is mainly used as an intermediate for pharmaceutical and chemical synthesis. If 2-bromo-5-chloroaniline is inhaled, move the patient to fresh air; if the skin comes into contact, take off contaminated clothing, rinse the skin thoroughly with soap and water, and seek medical treatment if you feel uncomfortable; if the eyes are clear In case of contact, separate eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse mouth immediately, do not induce vomiting, and seek medical attention immediately. Advice to protect rescuers is as follows: Move the patient to a safe place, consult a doctor, and if conditions permit, please show this chemical safety data sheet to the doctor who comes to the scene. If there is a small leak, collect the leaked liquid in a sealable container as much as possible, absorb it with sand, activated carbon or other inert materials, and transfer it to a safe place. Do not flush it into the sewer; if there is a large leak, build a dike or dig a pit. Contain, seal the drainage pipe, cover it with foam to inhibit evaporation, use an explosion-proof pump to transfer it to a tanker or a special collector, and recycle or transport it to a waste treatment site for disposal.

Structure

Apply^[1]

2-Bromo-5-chloroaniline can be used as an intermediate for pharmaceutical and chemical synthesis. For example, a solution of 2-bromo-5-chloroaniline (8.7 g, 42.3 mmol), acetic anhydride (13.06 g, 12.8 mmol) and a catalytic amount of DMAP in CH2Cl 2 (100 mL) was prepared at 0°C Stir down. The mixture was slowly warmed to 0°C. room temperature and stir overnight. The reaction mixture was washed with saturated aqueous NaHCO3 solution and concentrated. The residue was triturated with hexane/CH2Cl2, and the solid was filtered and rinsed with hexane to give the acetylated product (8.48 g, 80.7%).

Preparation ^[1]

A mixture of 1-bromo-4-chloro-2-nitro-benzene (10.0 g, 42.3 mmol) and SnCl2 (24.0 g, 127 mmol) in EtOAc (100 mL) was heated to reflux for 1 hour. After cooling to room temperature, water and NaHCO 3 were slowly added at 0°C until the reaction became alkaline. The mixture was filtered through celite and rinsed with EtOAc. The filtrate was washed with aqueous NaHCO3 and brine, dried (MgSO4), filtered and concentrated to give 2-bromo-5-chloroaniline (8.7 g, 100%) as black crystals.

Main reference materials

[1]Gavai, Ashvinikumar V.; Norris, Derek J.; Han, Wen-Ching; Vite, Gregory D.; Fink, Brian E.; Tokarski, John S. Patent: US2005/192310 A1, 2005; Location in patent: Page/Page column 22-23;