Chemical Properties
3-Bromoanisole, also known as m-Bromoanisole, is a clear colorless to pale yellow oily liquid. The boiling point is 210-211°C (100kPa), 105°C (2.13kPa), the relative density is 1.477, the refractive index is 1.5635, and the flash point is 93°C. It is soluble in alcohol, ether, benzene, and carbon disulfide, but insoluble in water. It is commonly used as a raw material for organic synthesis.
Uses
3-Bromoanisole used in chemical reaction as intermediates to obtain target materials such as dyes, pharmaceuticals, perfumes, photoinitiators and agrochemicals.
Preparation
3-Bromoanisole is synthesized through a reaction between m-bromophenol and dimethyl sulfate. The synthesis method involves the following steps:
Dissolve m-bromophenol in a sodium hydroxide solution.
Slowly add dimethyl sulfate dropwise to the solution while stirring.
Heat the mixture and allow it to react for 1 hour.
Cool the reaction mixture to separate the colorless oil formed.
Extract the water layer with ether.
Dry the ether extract and then distill it to recover the ether.
Distill the residue obtained after recovering the ether, along with the colorless oil, under reduced pressure.
This distillation process results in the production of m-bromoanisole as the final product.
The overall yield of m-bromoanisole achieved through this process is 90%.
Synthesis
GENERAL METHOD: A mixture of diaryliodonium salt (0.5 mmol), methylene halide (0.75 mmol) and acetonitrile (1 mL) was placed in a 10 mL reaction tube and heated at 80°C for 2 hours with vigorous stirring. After completion of the reaction (monitored by TLC or GC), the reaction mixture was cooled to room temperature and 5 mL of water was added. The mixture was stirred for 10 min and the product was extracted with ethyl acetate (3 x 10 mL). The organic layer was washed with water and dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with petroleum ether and ethyl acetate as eluents to give the pure m-bromoanisole. The structure of the product was confirmed by 1H NMR and 13C NMR analysis.
References
Application of Anisole, 2-Bromoanisole and 3-Bromoanisole as Overcharge Protection Additives in Lithium-Ion Batteries DOI:
10.6023/A12110964S. Ramalingam; S. Periandy. Spectroscopic investigation, computed IR intensity, Raman activity and vibrational frequency analysis on 3-bromoanisole using HF and DFT (LSDA/MPW1PW91) calculations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2011, 78 (2), 835-843. DOI:
10.1016/j.saa.2010.12.043Bobby Glover; Kimberly A. Harvey; Bing Liu; Matthew J. Sharp; and Maria F. Tymoschenko. Regioselective Palladium-Catalyzed Arylation of 3-Carboalkoxy Furan and Thiophene. Org. Lett. 2003, 5 (3), 301-304. DOI:
10.1021/ol027266q
