Application of 2-bromo-4-methyl-1-nitrobenzene_Kain Industrial Additive

Background and overview^[1][2]

2-Bromo-4-methyl-1-nitrobenzene can be used as a pharmaceutical and chemical synthesis intermediate. If 2-bromo-4-methyl-1-nitrobenzene is inhaled, move the patient to fresh air; if skin contact occurs, remove contaminated clothing and rinse the skin thoroughly with soap and water. If discomfort occurs , seek medical attention; if eye contact occurs, 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.

Apply^[1]

2-Bromo-4-methyl-1-nitrobenzene can be used as an intermediate for pharmaceutical and chemical synthesis, such as the synthesis of 2,5-bis(2-nitro-4-methylphenyl)-N-phenylpyrrole , the specific steps are: combine N-phenylpyrrole (0.54g, 8.0mmol), 2-bromo-4-methylnitrobenzene (0.40g, 2.0mmol), Cs₂CO ₃ The mixed system of (1.30g, 4mmol) and acetonitrile (30mL) was refluxed and stirred under nitrogen protection. After detecting the completion of the reaction by TLC, the system was cooled to room temperature, the solids in the system were removed by filtration, and the filtrate was collected. The filtrate was evaporated under reduced pressure and then subjected to flash column chromatography [silica gel, PE (petroleum ether)/DCM (dichloromethane)] for elution, and concentrated under reduced pressure to obtain a yellow solid 2,5-bis(2-nitro) -4-Tolyl)-N-phenylpyrrole, yield 80%.

Preparation ^[2]

The preparation of 2-bromo-4-methyl-1-nitrobenzene is as follows: at 70°C, under nitrogen protection, add 90% tert-butyl nitrite (1.47mL, 11.2mmol) and copper bromide ( E) Methyl-2-nitro-aniline (1.13g, 7.46mmol) in CH3CN (8mL) was added dropwise to a flask of CH3CN (40mL) (2.0g, 8.95mmol). After 20 min, the reaction was quenched by pouring into dilute HCl and the crude product was isolated by extraction with diethyl ether, dried over MgSO4 and concentrated in vacuo. Flash chromatography on silica gel gave the title compound 2-bromo-4-methyl-1-nitrobenzene (0.811 g, 50%).

Main reference materials

[1] CN101817774. A method for preparing 2-(2-nitrophenyl)pyrroles and 2,5-bis(2-nitrophenyl)pyrroles

[2] WO2007076035. ANTI-VIRAL COMPOUNDS