Synthetic technology of darifenacin intermediate 5-(2-bromomethyl)-2,3-dihydro-1-coumarone
A technology of alkyl and carbonyl, applied in the production of bulk chemicals, organic chemistry, etc., can solve the problems of unsuitable industrialization, high cost, low yield, etc., achieve high industrial application and economic value, increase the total yield, and improve the yield high effect
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[0036] Example 1: Preparation of compound of formula a-1
[0037]
[0038] Under the condition of -5~5℃, put anhydrous aluminum trichloride (215g, 1.62mol) and 770 ml of dichloromethane into the reaction flask, add acetyl chloride (95g, 1.22mol) dropwise, and then add dropwise 2. 3-Dihydrobenzofuran (97g, 0.81mol), continue to react for 2 to 2.5 hours after the addition is complete. After the reaction was completed, 1.5 L of ice water was added, the organic layer was separated, and washed with 400 ml of dilute hydrochloric acid and 400 ml of water successively. The organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated. 200ml of n-hexane was added for recrystallization, and a white solid was precipitated, which was dried to obtain 120g of a white solid compound of formula a-1 with a yield of 75.9%.
[0039]
Example Embodiment
[0040] Example 2: Preparation of compound of formula b-1
[0041]
[0042] Under nitrogen protection, add compound a-1 (5g, 0.025mol), sodium acetate 4.1 g, 0.05mol) and 50ml N,N-dimethylformamide, sodium iodide (0.1g, 0.6mmol), and heat to 120 ℃, TLC track until the reaction is complete. 50 ml of ethyl acetate was added for extraction, the organic phase was washed twice with 50 ml of water, and the organic layer was concentrated to obtain 5.1 g of compound of formula b with a yield of 92.7%.
[0043] 1 HNMR (400MHz, CDC1 3 ) δ=2.22(s,3H), δ=3.23 (t, J = 7.2 Hz, 2H), δ=4.64 (t, J = 7.2 Hz, 2H), δ=5.2(s, 2H), δ=6.81 (d, J=6.8Hz,2H), δ=7.72 (d, J=6.8Hz, 1H), 7.80 (s, lH) ;
[0044] MS: 243 (M + Na).
Example Embodiment
[0045] Example 3: Preparation of compound of formula b-1
[0046] Under the protection of nitrogen, add compound a -1 (5g, 0.025mol), acetic acid (3g, 0.05) and 50ml tetrahydrofuran, sodium iodide (0.1g, 0.6mmol) triethylamine (5.05g, 0.05), heat to reflux, TLC traces until the reaction is complete. Concentrate to remove tetrahydrofuran, add 50 ml of ethyl acetate for extraction, and then wash with 50 ml of water twice, and concentrate the organic layer to obtain 4.9 g of the compound of formula b with a yield of 89.1%.
[0047]
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