Midbody for preparing agomelatine and preparation method thereof
A kind of use and technology of phase transfer catalyst, which is applied in the direction of ether preparation, carboxylate preparation, and ester reaction to prepare ether, etc. It can solve the problems of difficult industrialization and expensive starting raw materials, and achieve high industrial application value and moderate reaction conditions , The effect of high product yield
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Embodiment 1
[0077] Embodiment 1: Preparation of 1-bromo-7-methoxynaphthalene
[0078] In the 250ml four-neck round bottom flask, add 1-bromo-7-naphthol (5.6g, 0.025mol) successively, 100ml toluene, dimethyl sulfate (15.8g, 0.125mol) and tetramethylammonium bromide (0.25g, 0.0015mol), start mechanical stirring. 14.0 g of 50% KOH aqueous solution was added dropwise at 25-40°C. After dripping, continue to react. The reaction was monitored by TLC until the conversion of the starting material 1-bromo-7-naphthol was complete. After the reaction, 10ml of water was added, the temperature was raised to 55-60°C, and the temperature was kept for 1 hour. Separate layers, take the upper organic phase and discard the lower aqueous phase. The organic phase was washed successively with 5% aqueous sodium hydroxide and 5% aqueous sodium chloride. The solvent was evaporated to dryness to obtain 5.39 g of 1-bromo-7-methoxynaphthalene as a colorless waxy solid, with a yield of 90.94%.
[0079] 1 H NMR ...
Embodiment 2
[0081] Embodiment 2: Preparation of 1-bromo-7-methoxynaphthalene
[0082] In the 1000ml four-neck round bottom flask, add 1-bromo-7-naphthol (22.3g, 0.10mol) successively, 400ml toluene, dimethyl sulfate (63.2g, 0.125mol) and tetrabutylammonium bromide (1.0g, 0.003mol) to start mechanical stirring. 56.0 g of 50% KOH aqueous solution was added dropwise at 10-15°C. After dripping, continue to react. The reaction was monitored by TLC until the conversion of the starting material 1-bromo-7-naphthol was complete. After the reaction, 100ml of water was added, the temperature was raised to 55-60°C, and the temperature was kept for 1 hour. Separate layers, take the upper organic phase and discard the lower aqueous phase. The organic phase was washed successively with 5% aqueous sodium hydroxide and 5% aqueous sodium chloride. The solvent was evaporated to dryness to obtain 22.52 g of 1-bromo-7-methoxynaphthalene as a colorless waxy solid, with a yield of 95.0%.
Embodiment 3
[0083] Embodiment 3: Preparation of 1-bromo-7-propoxynaphthalene
[0084] In the 250ml four-neck round bottom flask, add 1-bromo-7-naphthol (5.6g, 0.025mol) successively, 100ml toluene, dipropyl sulfate (22.8g, 0.125mol) and tetrapropylammonium bromide (0.4g, 0.0015mol), start mechanical stirring. 14.0 g of 50% KOH aqueous solution was added dropwise at 25-40°C. After dripping, continue to react. The reaction was monitored by TLC until the conversion of the starting material 1-bromo-7-naphthol was complete. After the reaction, 10ml of water was added, the temperature was raised to 55-60°C, and the temperature was kept for 1 hour. Separate layers, take the upper organic phase and discard the lower aqueous phase. The organic phase was washed successively with 5% aqueous sodium hydroxide and 5% aqueous sodium chloride. The solvent was evaporated to dryness to obtain 6.08 g of 1-bromo-7-propoxynaphthalene as a colorless waxy solid, with a yield of 91.83%.
[0085] MS (EI + ...
PUM
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