Process for producing 4-bromothioanisole
A technology of thioanisole and bromination, which is applied in the field of preparation of 4-bromothioanisole, and can solve the problems of difficult separation, low purity of the target product, and low yield
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Embodiment 1
[0026] In a 1-liter four-necked flask equipped with a stirrer, thermometer, dropping funnel and Liebig (Liebig) condenser, add 124.2g (1.00mol) thioanisole and 0.32g (0.002mol) ferrous chloride, 160 g (1.0 mol) of bromine was added dropwise to the flask at 50° C. under stirring for 4 hours. Subsequently, the reaction of the mixture was continued for 1 hour. After the reaction was completed, 50 g of water was added, and the organic layer was separated to obtain 202.9 g of crude 4-bromothioanisole. As determined by gas chromatography, the purity of the crude 4-bromothioanisole obtained by the aforementioned method was 90.3%.
[0027] Methanol (200.0 g) was added to the obtained crude 4-bromothioanisole, and the resulting mixture was slowly cooled from 50°C to -5°C under stirring to precipitate 4-bromothioanisole. The crystalline precipitate was collected by filtration and dried to obtain 158.4 g (0.78 mol, melting point 37.4-37.5° C.) of 4-bromothioanisole. The yield based on...
Embodiment 2
[0029] In a 1-liter four-neck flask equipped with a stirrer, thermometer, dropping funnel and Liebig condenser, 124.2g (1.00mol) thioanisole, 0.13g (0.001mol) aluminum chloride and 200g dichloro Methane, 160 g (1.0 mol) of bromine was added dropwise to the flask at 50° C. under stirring for 4 hours. Subsequently, the reaction of the mixture was continued for 2 hours. After the reaction was completed, 50 g of water was added for phase separation to obtain an organic layer containing 4-bromothioanisole. Dichloromethane in the obtained organic layer was distilled off to obtain 203.1 g of crude 4-bromothioanisole. As determined by gas chromatography, the purity of the crude 4-bromothioanisole obtained by this method is 90.1%.
[0030] Add a mixed solvent consisting of methanol and water (60% (weight) methanol) (300g) to the crude 4-bromothioanisole obtained, and slowly cool the resulting mixture from 50°C to -5°C under stirring, thereby 4-Bromothioanisole was precipitated. The...
Embodiment 3
[0032] In a 1-liter four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a Liebig condenser, add 124.2g (1.00mol) of thioanisole and 0.068g (0.001mol) of boron trifluoride at 50°C Add 160 g (1.0 mol) of bromine dropwise to the flask with stirring for 4 hours. Subsequently, the reaction was continued for 1 hour. After the reaction was completed, 50 g of water was added, and the organic layer was separated to obtain 203.9 g of crude 4-bromothioanisole. As determined by gas chromatography, the purity of the crude 4-bromothioanisole obtained by this method is 90.5%.
[0033] Methanol (200.0 g) was added to the obtained crude 4-bromothioanisole, and the resulting mixture was slowly cooled from 50°C to -5°C under stirring to precipitate 4-bromothioanisole. The crystalline precipitate was collected by filtration and dried to obtain 159.5 g (0.785 mol) of 4-bromothioanisole. The yield based on thioanisole was 78.5%. As determined by gas chromatography, t...
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