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CAS No. : | 76-83-5 | MDL No. : | MFCD00000813 |
Formula : | C19H15Cl | Boiling Point : | - |
Linear Structure Formula : | CCl(C6H5)3 | InChI Key : | JBWKIWSBJXDJDT-UHFFFAOYSA-N |
M.W : | 278.77 | Pubchem ID : | 6456 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310-P405-P501 | UN#: | 3261 |
Hazard Statements: | H314 | Packing Group: | Ⅱ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With triethylamine In tetrahydrofuran; dichloromethane at 20℃; for 1 h; | To a single-necked flask was added 4-bromoimidazole (30 g, 205 mmol)Dichloromethane: tetrahydrofuran = 1: 1,And triphenylchloromethane (62 g, 226 mmol)Triethylamine (29 ml) was added with stirring at room temperature,Continue stirring for 1 h, add water and 1N hydrochloric acid,Adding methylene chloride extraction,The organic layers were combined and dried over anhydrous sodium sulfate,Spin dry dichloromethane to give compound 7 (61g, 72percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 6 h; | General procedure: The 4-hydroxybenzaldehyde 4 (0.8 g, 6.5 mmol) was reacted with 4-monometoxytriphenylmethyl (1.0 g, 3.2 mmol) in 10 mL of anhydrous DCM in the presence of DIEA (2.2 mL, 12.9 mmol). After 6 h at r.t., the reaction was quenched by dilution with DCM (100 mL), and the organic phase was washed three times with a solution of 0.1 M NaOH (3×100 mL). The organic phase was dried with MgSO4, and then the solvent was removed under vacuum. The crude material was then purified on a column of silica gel (70 g) suspended in hexane/EtOAc 70:30 (v/v) with 1percent of TEA, leading to product 5 (1.05 g, 82percent). 1H NMR (400 MHz, 25°C, δ, ppm in CDCl3): δ 9.76 (s, 1H), 7.57–7.25 (complex signals, 14H), 6.86 (d, J=8.5 Hz, 2H), 6.82 (d, J=8.0 Hz, 2H), 3.77 (s, 3H). 13C NMR (100 MHz, 25°C, δ, ppm in CDCl3): δ 190.7, 161.9, 158.7, 143.8, 134.9, 130.6, 130.2, 128.3, 127.8, 127.3, 120.3, 113.1, 91.1, 55.0. Product 5 (1.05 g, 2.66 mmol) was subsequently treated with 0.25 g of NaBH4 (6.60 mmol) in THF (10 mL) for 6 h at r.t. The mixture was diluted with DCM (3×100 mL), and the organic phase was washed three times with water (100 mL). The organic phase was dried with MgSO4, and then the solvent was removed under vacuum. The crude solid thus obtained was purified on a column of silica gel (70 g) suspended in hexane/EtOAc 60:40 (v/v) with 1percent of TEA. From the column was recovered 0.845 g of clean desired product 6 (2.13 mmol, 80percent). 1H NMR (400 MHz, 25°C, δ, ppm in CDCl3): δ 7.49 (d, J=6.0 Hz, 4H), 7.37–7.22 (complex signals, 8H), 6.98 (d, J=7.2 Hz, 2H), 6.79 (d, J=7.2 Hz, 2H), 6.70 (d, J=6.8 Hz, 2H), 4.45 (s, 2H), 3.75 (s, 3H). 13C NMR (100 MHz, 25°C, δ, ppm in CDCl3): δ 158.4, 155.8, 144.5, 135.6, 133.3, 130.4, 128.6, 127.6, 127.4, 126.9, 120.6, 112.8, 90.0, 64.8, 55.0. Then, 0.40 g (1.01 mmol) of product 6 was reacted with N,N-diisopropyldichlorophosphoramidite (124 μL, 0.67 mmol) in the presence of DIEA (348 μL, 2.68 mmol) in DCM (7 mL). After 1.5 h, the reaction was quenched by dilution with DCM, and the organic phase was washed three times with cold water. The organic phase was dried with MgSO4 and the solvent removed under vacuum. The material was purified with column chromatography of silica gel in hexane/EtOAc 85:15 (v/v) with 2percent of TEA. From the column was recovered 0.74 g of clean desired product (1, 87percent). |
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