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Chemical Structure| 586373-70-8 Chemical Structure| 586373-70-8

Structure of 586373-70-8

Chemical Structure| 586373-70-8

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Product Details of [ 586373-70-8 ]

CAS No. :586373-70-8
Formula : C8H9ClO2S
M.W : 204.67
SMILES Code : CS(=O)(=O)C1=CC=CC(CCl)=C1
MDL No. :MFCD12025161

Safety of [ 586373-70-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3261
Packing Group:

Application In Synthesis of [ 586373-70-8 ]

* 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 [ 586373-70-8 ]

[ 586373-70-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 220798-39-0 ]
  • [ 586373-70-8 ]
YieldReaction ConditionsOperation in experiment
95% With thionyl chloride; at 80℃; for 3h; A solution of (3-methanesulfonyl) phenyl methanol (0.21 g, 1.1 mmol) in thionyl chloride (3 ML) was heated at 80C for 3 h. The reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure to provide 1-CHLOROMETHYL-3- methanesulfonylbenzene as a yellow oil (0.23 g, 95%) : 1H NMR (300 MHz, CDCl3) 8 7.98 (s, 1H), 7.90 (d, J = 8 Hz, 1H), 7.70 (d, J = 8 Hz, 1H), 7.59 (t, J = 8 Hz, 1H), 4.65 (s, 2H), 3.08 (s, 3H).
77% With tetrachloromethane; triphenylphosphine; In tetrahydrofuran; at 20 - 75℃; Triphenylphosphine (7.5 g, 29 mmol), carbon tetrachloride (11.0 ml_, 114 mmol) and tetrahydrofuran (18 ml_) were combined and stirred at room temperature for 10 minutes. A suspension of <strong>[220798-39-0](3-methanesulfonyl-phenyl)-methanol</strong> (2.68 g, 14.3 mmol) in 18 ml_ tetrahydrofuran was added, then the reaction mixture was heated at 75 C for 3 hours. The reaction mixture was cooled to room temperature, then partitioned between ethyl acetate and water. The organic phase was dried over MgSO4, filtered, and concentrated to give the crude product as an oily solid. A solution of this crude product and dichloromethane was evaporated over silica gel, and the resulting silica gel supported crude product was loaded onto an Analogix SuperFlash column. Flash chromatography (15% - 35% ethyl acetate in hexanes) afforded 2.26 g (77%) of 3-(methanesulfonyl)benzyl chloride as a white solid. 1H NMR (300 MHz, DMSO- Cf6) delta ppm 8.01 (s, 1 H), 7.91 (d, J = 7.8 Hz, 1 H), 7.81 (d, J = 7.8 Hz, 1 H), 7.68 (t, J = 7.8 Hz, 1 H), 4.90 (s, 2 H), 3.24 (s, 3 H). HRMS (El+) cald. for C8H9CIO2S [M+] 204.0012, obsd. 204.0012.
With methanesulfonyl chloride; triethylamine; In dichloromethane; at 20 - 50℃; for 4h; 0.267 ml (3.45 mmol) METHANESULPHONYL-CHLORIDE is added to o a solution of 584 mg (3.14 mmol) (3-METHANESULPHONYL-PHENYL)-METHANOL and 0.66 ml (4.71 mmol) triethylamine in 6 ml dichloromethane. This reaction mixture is stirred at room tem- perature for 1 h and at 50 C FOR additional 3 h. The reaction mixture is then poured into water and extracted twice with dichloromethane. The combined organic layers are washed with water and brine, dried, filtered and concentrated in vacuo to afford the title compound, which is used in the next step without further purification. 'H-NMR (300 MHz, DMSO): 7.98 (broad s, 1H), 7. 86 (d, 1H), 7.77 (d, 2H), 7.64 (t, 1H), 4. 86 (s, 2H), 3.21 (s, 3H).
With methanesulfonyl chloride; triethylamine; In dichloromethane; for 16h; Borane solution (1M in THF) was added dropwise to a stirred mixture of 3-methylsulfonyl)benzoic acid (400 mg, 2.00 mmol) in anhydrous THF (2 ml) at 0 C. The resulting mixture was then allowed to warm to room temperature and stirred for 3 h. The reaction mixture quenched with water/1 M HCl (aq.), extracted with ethyl acetate (3 times), the combined organic extracts dried (sodium sulfate) and concentrated in vacuo to give crude <strong>[220798-39-0](3-(methylsulphonyl)phenyl)methanol</strong> as an oil which was used in the next step without further purification. The alcohol was dissolved in dichloromethane (6 ml) and triethylamine (0.418 mL, 3.0 mmol). Methanesulfonylchloride (first batch (0.186 mL, 2.4 mmol) was then added, followed by a second batch (0.039 mL, 0.5 mmol) and the resulting mixture was stirred for 16 h. 1 N HCl solution (aq.) was then added and the reaction mixture was extracted with diethyl ether (3 times), the combined organic extracts were dried (sodium sulfate) and concentrated in vacuo. The residue was purified by column chromatography eluting using a gradient (petroleum ether 40/60/ethyl acetate 1:0 v/v 0:1) to afford 212 mg (52% over 2 steps) of the title compound as an oil. 1H NMR (CDCl3): 7.98 (1H, s), 7.91 (1H, d, J 7.8), 7.70 (1H, d, J 7.8), 7.59 (1H, t, J 7.8), 4.65 (2H, s), 3.08 (s, 3H).
With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 - 26℃; for 16h; To a cold (0 C) solution of Intermediate AY (2g, 10.75 mmol) and triethylamine (2.26 mL, 16.12 mmol) in dichloromethane (25 mL) was added slowly methanesulfonyl chloride (1.08 mL, 13.85 mmol) over 5 minutes. After the addition was complete, the reaction mixture was allowed to reach room temperature and stirred for 16 hours. The reaction mixture was quenched with cold water (10 mL), diluted with dichloromethane (20 mL), washed with cold water (2 chi 50 mL) and brine (20 mL), dried over anhydrous Na2S04, and the solvent was removed to afford the crude Intermediate AZ. This material was purified by column chromatography (silica gel 100-200 mesh) using 10% ethyl acetate in petroleum ether as the eluent to afford the product (1.6g, 73%) as a pale yellow oil. NMR (CDC13): delta 7.98 (s, 1H), 7.91 (d, J = 7.80 Hz; 1H), 7.70 (d, J= 7.80 Hz, 1H), 7.59 (t, J= 7.80 Hz; 1H), 4.65 (s, 2H), 3.07 (s, 3H). Mass (M+H): 205.0.
With thionyl chloride; In dichloromethane; for 2h; A suspension of <strong>[220798-39-0](3-(methylsulfonyl)phenyl)methanol</strong> (0.106 g, 0.569 mmol) in dry dichloromethane (3.0 mL) was treated with thionyl chloride (0.249 mL, 3.42 mmol) and the mixture was stirred for 2 hours, during which time all solids dissolved. The reaction was concentrated under reduced pressure and the residue was dried twice from dichloromethane. The residue was used immediately in the following experiment. 1H NMR (400 MHz, CDCl3) delta: 8.07-7.88 (m, 2H), 7.77-7.54 (m, 2H), 5.22-4.99 (m, 1H), 4.66 (s, 1H), 3.10-3.06 (m, 3H).

 

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