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Chemical Structure| 1455091-04-9 Chemical Structure| 1455091-04-9

Structure of 1455091-04-9

Chemical Structure| 1455091-04-9

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Product Details of [ 1455091-04-9 ]

CAS No. :1455091-04-9
Formula : C15H13ClO3
M.W : 276.72
SMILES Code : O=C(OC)C1=CC=C(OC2=CC=CC=C2)C=C1CCl
MDL No. :MFCD29075435

Safety of [ 1455091-04-9 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501
Class:8
UN#:3261
Packing Group:

Application In Synthesis of [ 1455091-04-9 ]

* 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.

  • Downstream synthetic route of [ 1455091-04-9 ]

[ 1455091-04-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1455091-04-9 ]
  • [ 1455091-10-7 ]
  • 2
  • [ 67-56-1 ]
  • [ 57830-14-5 ]
  • [ 1455091-04-9 ]
YieldReaction ConditionsOperation in experiment
83% <strong>[57830-14-5]5-phenoxyisobenzofuran-1(3H)-one</strong> (1.0g, 4.42mmol), xylene 10mL, benzyl triethyl ammonium chloride (300 mg, 1.32 mmol) and boron trifluoride diethyl ether (200 mg, 1.41 mmol) were added to the reaction flask, and the mixture was heated to 100 C dropwise to add thionyl chloride (5.0 g, 42.03 mmol). The reaction was carried out at 135 C for 5 hours. After the reaction was completed by thin layer chromatography, the filtrate was concentrated under reduced pressure. The filtrate was concentrated to 3 mL of methanol. The mixture was stirred at 55 C for 1 hour, then concentrated to dryness under reduced pressure. The potassium carbonate solution and the sodium chloride solution were washed and concentrated to dryness to give the title compound 2c (1.0 g, 83.0%).Used directly in the next step.
87.02 g To a solid mixture of 5-phenoxy-3H-isobenzofuran-l-one (65.54 g, 0.29 mol), boric acid (538 mg, 8.7 mmol) and triphenylphosphine oxide (2.42 g, 8.7 mmol) was added thionyl chloride (42.3 mL). The resulting mixture was refluxed overnight. After cooled, methanol (300 mL) was slowly added to the reaction mixture. It was then refluxed for 1 h and concentrated. Residue was partitioned between EtOAc and saturated NaHC03 solution. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated to provide the title compound (87.02 g, 0.31 mol) as an oil. It was used directly to the next reaction without further purification. lH NMR in CDCI3, delta in ppm: 7.91 (d, 1 H, 8.6 Hz), 7.5-6.9 (m, 7 H), 5.06 (s, 2 H), 3.83 (s, 3 H).
102351 A reactor was charged with toluene (24 Kg), and stirring was initiated. The reactor was then charged with <strong>[57830-14-5]5-phenoxyphthalide</strong> (56 Kg), thionyl chloride (41 Kg), trimethyl borate (1 Kg), dichlorotriphenylphosphorane (2.5 Kg), and potassium carbonate (77 Kg). The mixture was heated to reflux until reaction completion and solvent was removed leaving 2-chloromethyl-4-phenoxybenzoylchloride. Methanol was charged and the mixture was heated above 50 C until reaction completion. Solvent was removed and replaced with DMF. This solution of the product methyl 2-chloromethyl-4- phenoxybenzoic acid methyl ester in DMF was used directly in the next step (HPLC: 85%).
  • 3
  • [ 1455091-04-9 ]
  • [ 2645-02-5 ]
  • [ 1455091-10-7 ]
YieldReaction ConditionsOperation in experiment
72.5% Methyl 2-(chloromethyl)-4-phenoxybenzoate (0.68 g, 2.46 mmol),N-p-toluenesulfonylglycine methyl ester (0.7 g, 2.88 mmol), potassium carbonate (0.68 g, 4.923 mmol), potassium iodide (0.16 g, 0.96 mmol), DMF was added to the reaction flask, replaced with nitrogen, and heated to 50 C. After reacting for 1 hour, 2 mL of methanolic sodium methoxide solution was added to room temperature and stirred for 30 min. After the reaction was completed by thin layer chromatography, 40 mL of purified water was added to the reaction mixture, and glacial acetic acid was added dropwise with stirring to adjust pH=7, suction filtration, and the filter cake was added with acetone. 4 mL was stirred for 2 hours, and suction filtered to give the title compound 2d (525 mg, 72.5%).
102361 A reactor was charged with a solution of 2-chloromethyl-4-phenoxybenzoic acid methyl ester (68 Kg) in DMF, and stirring was initiated. The reactor was then charged with p-toluenesulfonylglycine methyl ester (66 Kg), potassium carbonate (60 Kg), and sodium iodide (4 Kg). The mixture was heated to at least 50 C until reaction completion. The mixture was cooled. Sodium methoxide in methanol was charged and the mixture was stirred until reaction completion. Acetic acid and water were added, and themixture was stirred, filtered and washed with water. Solid was purified by acetone trituration and dried inan oven giving 3a (Yield from step b): 58%; HPLC: 99.4%). ?H NMR (200 MHz, DMSO-d6) d 11.60 (s,1 H), 8.74 (s, 1H), 8.32 (d, J = 9.0 Hz, 1 H), 7.60 (dd, J = 2.3 & 9.0 Hz, 1H), 7.49 (m, 3 H), 7.24 (m, 3 H),3.96 (s, 3 H); MS-(+)-ion M+1 = 296.09
 

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