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[ CAS No. 15258-73-8 ]

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Chemical Structure| 15258-73-8
Chemical Structure| 15258-73-8
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CAS No. :15258-73-8 MDL No. :MFCD00004609
Formula : C7H6Cl2O Boiling Point : 268.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :177.03 g/mol Pubchem ID :27156
Synonyms :

Safety of [ 15258-73-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 15258-73-8 ]

  • Upstream synthesis route of [ 15258-73-8 ]
  • Downstream synthetic route of [ 15258-73-8 ]

[ 15258-73-8 ] Synthesis Path-Upstream   1~8

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YieldReaction ConditionsOperation in experiment
94% With sodium tetrahydroborate In ethanol at 20℃; for 2 h; To a solution of 3,5-dichlorobenzaldehyde (340 mg, 1.94 mmol) in ethanol (4 mL)Sodium borohydride (74 mg, 1.94 mmol) was added.After stirring at room temperature for 2 hours, 1N hydrochloric acid was added to quench the reaction. The solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate (10 mL), washed with 1N hydrochloric acid and then water (10 mL×2), and the organic phase was dried over anhydrous sodium sulfate. After concentration, the product 3-e (320 mg) was obtained. 94percent).
90%
Stage #1: With Triethoxysilane; [cis-Fe(H)(SPh)(PMe3)4] In tetrahydrofuran at 50℃; for 2 h;
Stage #2: With methanol; sodium hydroxide In tetrahydrofuran; water at 60℃; for 24 h;
General procedure: To a 25 mL Schlenk tube containing a solution of 1 in 2 mL of THF was added an aldehyde (1.0 mmol) and (EtO)3 SiH (0.20 g, 1.2 mmol). The reaction mixture was stirred at 50–55 °C until there was no aldehyde left (monitored by TLC and GC–MS). The reaction was then quenched byMeOH (2mL) and a 10percent aqueous solution of NaOH (5 mL) with vigorous stirring at 60 °C for about 24 h.The organic product was extracted with diethyl ether (10 mL × 3), dried over anhydrous MgSO4, and concentrated under vacuum. The alcohol product was further purified using flash column chromatography (elute with 5–10percent ethyl acetate in petroleum ether). The 1H NMR and 13C NMR spectra of the alcohol products are providedin Supporting information.
90% With Triethoxysilane; potassium phenyltrifluoborate In methanol at 20℃; for 0.166667 h; Take a 25mL reaction bottle,Place a magnet in the bottle.Weigh 2,6-dichlorobenzaldehyde (0.131 g, 0.75 mmol),Potassium phenyl trifluoroborate (2.5percent eq. 3.5 mg),Add 3 mL of methanol to the reaction flask as a solvent.The pipette was then used to remove trimethoxysilane (2.2 eq. 202 μL).The reaction is carried out in an air atmosphere at room temperature.The progress of the reaction was detected by TLC.After 10 minutes, it was extracted with dichloromethane (3×40 mL).The dichloromethane phases were combined and washed with 40 mL of deionized water.Dry over anhydrous sodium sulfate,Rotary evaporation to remove the solvent,Column chromatography gave 120 mg of the product as a white solid.Yield 90percent;The NMR is as follows:
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[5] Patent: CN109020779, 2018, A, . Location in patent: Paragraph 0049; 0050
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[7] Tetrahedron Letters, 1983, vol. 24, # 40, p. 4287 - 4290
[8] Dalton Transactions, 2014, vol. 43, # 30, p. 11716 - 11722
[9] RSC Advances, 2018, vol. 8, # 25, p. 14092 - 14099
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[11] Journal of Organic Chemistry, 1999, vol. 64, # 9, p. 3230 - 3236
[12] Journal of Organic Chemistry, 1956, vol. 21, p. 142
[13] Chemical and pharmaceutical bulletin, 1967, vol. 15, # 12, p. 1990 - 1995
[14] Organometallics, 2013, vol. 32, # 18, p. 5235 - 5238
[15] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5781 - 5788
[16] ACS Catalysis, 2015, vol. 5, # 9, p. 5540 - 5544
[17] Journal of the American Chemical Society, 2014, vol. 136, # 45, p. 15813 - 15816
[18] Organometallics, 2016, vol. 35, # 20, p. 3538 - 3545
[19] Catalysis Science and Technology, 2017, vol. 7, # 13, p. 2828 - 2837
[20] Patent: WO2017/212289, 2017, A1, . Location in patent: Page/Page column 19; 20
[21] Dalton Transactions, 2018, vol. 47, # 12, p. 4352 - 4359
[22] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3145 - 3157
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[24] New Journal of Chemistry, 2018, vol. 42, # 20, p. 16583 - 16590
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YieldReaction ConditionsOperation in experiment
95% With zinc(II) tetrahydroborate In ethanol at 78℃; for 3 h; Add 100 ml of absolute ethanol to the four-necked flask and heat to reflux.15 g of the raw material methyl 2,6-dichlorobenzoate was added to the ethanol.10 g of zinc borohydride was slowly added thereto, and the reaction was stirred at 78 ° C for 3 h.After the GC reaction was completed, the solvent was evaporated to dryness to obtain 12 g.2,6-dichlorobenzyl alcohol.The product yield was 95percent and the purity was 98percent.
Reference: [1] Patent: CN108794297, 2018, A, . Location in patent: Paragraph 0007; 0008; 0009
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Reference: [1] Synthesis (Germany), 2012, vol. 44, # 14, p. 2237 - 2242
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  • [ 17849-38-6 ]
Reference: [1] Catalysis Communications, 2016, vol. 87, p. 78 - 81
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  • [ 20443-98-5 ]
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Reference: [1] Tetrahedron, 1974, vol. 30, # 15, p. 2467 - 2475
[2] Journal of Organic Chemistry, 1991, vol. 56, # 1, p. 264 - 267
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Reference: [1] Catalysis Science and Technology, 2017, vol. 7, # 11, p. 2165 - 2169
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Reference: [1] Journal of Organic Chemistry, 1956, vol. 21, p. 142
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 10, p. 2729 - 2734
[2] Tetrahedron Letters, 1988, vol. 29, # 6, p. 707 - 710
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