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Chemical Structure| 99768-21-5 Chemical Structure| 99768-21-5

Structure of 99768-21-5

Chemical Structure| 99768-21-5

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Product Details of [ 99768-21-5 ]

CAS No. :99768-21-5
Formula : C8H9BrO2S
M.W : 249.13
SMILES Code : O=S(C1=CC=C(Br)C=C1C)(C)=O
MDL No. :MFCD22549347
InChI Key :LNVYXKNXYRIPOR-UHFFFAOYSA-N
Pubchem ID :20616765

Safety of [ 99768-21-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 99768-21-5 ]

* 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 [ 99768-21-5 ]

[ 99768-21-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 89981-03-3 ]
  • [ 99768-21-5 ]
  • 3
  • [ 116632-39-4 ]
  • [ 20277-69-4 ]
  • [ 99768-21-5 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; In dimethyl sulfoxide; at 100 - 125℃; for 3.33333h;Microwave irradiation; A mixture of 4-bromo-1-iodo-2-methylbenzene (240 μL, 1.68 mmol, Aldrich), Copper(I) iodide (353 mg, 1.85 mmol, Alfa Aesar), Methanesulfinic acid, sodium salt (688 mg, 6.74 mmol, Alfa Aesar) and DMSO (7.2 mL) was purged with Argon and then heated under microwave condition at 125 C. for 20 min. The resulting mixture was stirred at 100 C. for 3 h and then cooled to room temperature. The reaction mixture was diluted with H2O and extracted with EtOAc (2×). The organic layers were combined and washed with brine, dried over Na2SO4 and concentrated in vacuo to a white solid. The solid was purified by flash chromatography (SiO2, 0-50% EtOAc in hexanes) to yield 270 mg of desired product as a white solid. MS (ESI) 249 (M+H).
  • 4
  • [ 1101873-47-5 ]
  • [ 99768-21-5 ]
  • [ 1104450-19-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;copper(l) iodide; 8-quinolinol; In dimethyl sulfoxide; at 140℃; A mixture of <strong>[99768-21-5]4-bromo-2-methyl-1-(methylsulfonyl)benzene</strong> (79 mg, 0.32 mmol), 4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one (100 mg, 0.318 mmol), quinolin-8-ol (18.5 mg, 0.127 mmol, Alfa Aesar), potassium carbonate (57.1 mg, 0.414 mmol), Copper(I) iodide (24.2 mg, 0.127 mmol, Alfa Aesar) in DMSO (4 mL) was stirred under Ar at 140 C. overnight. The resulting mixture was diluted with H2O and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to a green oil. The oil was purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2) to yield 107.7 mg of desired product as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.10-8.22 (m, 3 H), 7.34-7.43 (m, 2 H), 7.18 (d, J=7.82 Hz, 1 H), 6.03 (dd, J=7.58, 2.20 Hz, 1 H), 5.99 (d, J=2.45 Hz, 1 H), 4.47-4.63 (m, 1 H), 4.13-4.22 (m, 2 H), 3.56-3.69 (m, 2 H), 3.09 (s, 3 H), 2.73 (s, 3 H), 2.39 (t, J=7.58 Hz, 2 H,) 2.00-2.12 (m, 2 H), 1.75-1.92 (m, 2 H), 1.47-1.62 (m, 2 H), 0.92 (t, J=7.34 Hz, 3 H). MS (ESI) 483 (M+H).
  • 5
  • [ 139937-37-4 ]
  • [ 79-08-3 ]
  • [ 99768-21-5 ]
YieldReaction ConditionsOperation in experiment
205 mg 4-Bromo-2-methyl-l-(methylsulfonyl)benzene for Example 35235 mg Sodium sulfite and 470 mg NaHC03 were dissolved in 1.75 mL of water and heated to 75C. 500 mg of 4-Bromo-2-methyl-benzenesulfonyl chloride were added in portions within 10 min (gas formation) and the mixture stirred for 1 h at 75C. 387 mg of Bromoacetic acid and 150 of water was added in small portions and the mixture stirred at 105C overnight. After cooling to 25C the mixture was acidified to pH 1 using 4N HCl. The resulting precipitate was collected and washed with water to yield 205 mg solid.Analysis: HPLC-MS: Rt = 0.73 (method X001 002) M+H = 249/251
205 mg 4.1.4.1. Synthesis of R2-Hal 4-Bromo-2-methyl-1-(methylsulfonyl)benzene for Example 35[0181] Sodium sulfite and 470 mg NaHCO3 were dissolved in 1.75 mL of water and heated to 75 C. 500 mg of 4-Bromo-2-methyl-benzenesulfonyl chloride were added in portions within 10 min (gas formation) and the mixture stirred for 1 h at 75 C. 387 mg of Bromoacetic acid and 150 μL of water was added in small portions and the mixture stirred at 105 C. overnight. After cooling to 25 C. the mixture was acidified to pH 1 using 4N HCl. The resulting precipitate was collected and washed with water to yield 205 mg solid.[0183]Analysis: HPLC-MS: Rt=0.73 (method X001-002) M+H=249/251
 

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