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[ CAS No. 1535-65-5 ]

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Chemical Structure| 1535-65-5
Chemical Structure| 1535-65-5
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CAS No. :1535-65-5 MDL No. :MFCD01050170
Formula : C7H6F2O2S Boiling Point : 289.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :192.18 g/mol Pubchem ID :11816356
Synonyms :

Safety of [ 1535-65-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
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  • Upstream synthesis route of [ 1535-65-5 ]
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[ 1535-65-5 ] Synthesis Path-Upstream   1~22

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Reference: [1] Chemical Communications, 2007, # 48, p. 5149 - 5151
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  • [ 175676-65-0 ]
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Reference: [1] Chemical Communications, 2016, vol. 52, # 18, p. 3657 - 3660
[2] Chemical Communications, 2016, vol. 52, # 18, p. 3657 - 3660
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  • [ 1535-67-7 ]
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YieldReaction ConditionsOperation in experiment
88% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 24 h; To a solution of difluoromethyl phenyl sulfide 2 (3.98 g, 25 mmol) in dry CH2Cl2 (69 mL) at 0°C, a solid m-CPBA (15.9 g, 92.0 mmol) was added portionwise. The reaction was then warmed to room temperature and left for overnight stirring. CH2Cl2 (50 mL) was then added and the mixture was washed with 10percent aqueous Na2SO3 (2 100 mL), 5percent aqueous NaHCO3 (4 50 mL) and brine(2 100 mL), respectively. Organic layer was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using CH2Cl2 and hexane as eluents (3:1). Rf = 0.40 (CH2Cl2/hexane, 3:1).Yield: 4.24 g, 22.1 mmol, 88percent. 1H NMR (300 MHz, CDCl3): d 8.01 (dt, J = 8.7; 1.7 Hz, 2H, HAr),7.85–7.78 (m, 1H, HAr), 7.72–7.62 (m, 2H, HAr), 6.20 (t, J = 53.4 Hz,1H, CF2H); 13C NMR (101 MHz, CDCl3): d 136.0 (s, CAr), 131.9 (s,CAr), 130.8 (s, CAr), 129.7 (s, CAr), 114.8 (t, J = 285.9 Hz, CF2H); 19FNMR (282 MHz, CDCl3): d 122.1 (d, J = 53.4 Hz, 2F, CF2H). TheNMR data were in a good agreement with those already reported.
83% With 3-chloro-benzenecarboperoxoic acid In dichloromethane EXAMPLE 2
Difluoromethyl Phenyl Sulfone
A solution of 2.0 g (12 mmol) of difluoromethyl phenyl sulfide in 20 mL of dichloromethane was cooled to 0°-5° C. and treated portionwise with 5.4 g (27 mmol) of 85percent meta-chloroperbenzoic acid.
The mixture was allowed to warm to room temperature, stirred for 4 hours, treated with an additional 1.1 g (5.4 mmol) of 85percent meta-chloroperbenzoic acid, and stirred overnight.
Filtration and washing of the filter cake with 30 mL of dichloromethane gave a solution which was washed with three 25 mL portions of saturated NaHCO3 and one 25 mL portion of water, dried (MgSO4), and concentrated in vacuo.
The residue was purified by flash chromatography on 50 g of silica gel (eluted with 25percent dichloromethane, 75percent petroleum ether) to give 1.92 g (83percent yield) of difluoromethyl phenyl sulfone as a colorless liquid: IR (neat) 3069, 1771, 1447, 1348, 1301, 1162, 1113, 1077, 760, 725, 685, 621, 606, 557, 545, 515,
cm-1; 1 H NMR (CDCl3) δ6.29 (t, 1H, JHF =54Hz), 7.50-8.10 (m, 5H); mass spectrum (70 eV) m/e (relative intensity) 192 (22, M+), 141 (45), 77 (100), 51 (54).
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 7, p. 1827 - 1831[2] Angew. Chem., 2014, vol. 126, # 7, p. 1858 - 1862,5
[3] Journal of Fluorine Chemistry, 2015, vol. 179, p. 175 - 178
[4] Patent: US4837327, 1989, A,
[5] Journal of the American Chemical Society, 1960, vol. 82, p. 6178 - 6181
[6] Journal of Fluorine Chemistry, 1989, vol. 43, p. 53 - 66
[7] Journal of Fluorine Chemistry, 2007, vol. 128, # 10, p. 1098 - 1103
[8] Organic Letters, 2016, vol. 18, # 22, p. 5912 - 5915
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YieldReaction ConditionsOperation in experiment
71% With n-butyllithium; chloro-trimethyl-silane In tetrahydrofuran at -78℃; for 6 h; To a solution of bromodifluoromethyl phenyl sulfone 9 (0.54 g, 2.00 mmol) and TMSCl (0.38 mL, 3.00 mmol) in dry THF cooled to -78 °C was added dropwise n-BuLi (1.6 M, 2.25 mL, 3.60 mmol). Reaction was stirred for 6 h at -78 °C. Saturated aqueous NH4Cl 15mL) was then added at -78 °C, the residue was brought to room temperature and extracted with Et2O (3 15 mL). The combined organic layers were washed with brine, water, then dried (Na2SO4) and concentrated under reduced pressure.The crude product was purified by silica gel column chromatography using CH2Cl2 and hexane as eluents (3:2). Rf = 0.38 (CH2Cl2/hexane,3:2).Yield: 0.27 g, 1.4 mmol, 71percent.
Reference: [1] European Journal of Organic Chemistry, 2012, # 30, p. 5943 - 5952,10
[2] European Journal of Organic Chemistry, 2012, # 30, p. 5943 - 5952
[3] Journal of Fluorine Chemistry, 2015, vol. 179, p. 175 - 178
[4] Tetrahedron Letters, 2005, vol. 46, # 48, p. 8273 - 8277
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Reference: [1] RSC Advances, 2016, vol. 6, # 85, p. 82298 - 82300
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Reference: [1] Journal of Fluorine Chemistry, 2007, vol. 128, # 10, p. 1098 - 1103
[2] European Journal of Organic Chemistry, 2012, # 30, p. 5943 - 5952,10
[3] European Journal of Organic Chemistry, 2012, # 30, p. 5943 - 5952
[4] Angewandte Chemie - International Edition, 2014, vol. 53, # 7, p. 1827 - 1831[5] Angew. Chem., 2014, vol. 126, # 7, p. 1858 - 1862,5
[6] Journal of Fluorine Chemistry, 2015, vol. 179, p. 175 - 178
[7] Journal of Fluorine Chemistry, 2015, vol. 179, p. 175 - 178
[8] Organic Letters, 2016, vol. 18, # 22, p. 5912 - 5915
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Reference: [1] Helvetica Chimica Acta, 2012, vol. 95, # 10, p. 2043 - 2051
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Reference: [1] Synthesis, 2010, # 11, p. 1883 - 1890
[2] Tetrahedron Letters, 2005, vol. 46, # 48, p. 8273 - 8277
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Reference: [1] European Journal of Organic Chemistry, 2012, # 30, p. 5943 - 5952,10
[2] European Journal of Organic Chemistry, 2012, # 30, p. 5943 - 5952
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Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 47, p. 12390 - 12394[2] Angew. Chem., 2013, vol. 125, # 47, p. 12616 - 12620,5
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Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 24, p. 9046 - 9052
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Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, # 13, p. 3023 - 3027
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Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 33, p. 3184 - 3187
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Reference: [1] European Journal of Organic Chemistry, 2012, # 30, p. 5943 - 5952,10
[2] European Journal of Organic Chemistry, 2012, # 30, p. 5943 - 5952
[3] Journal of Fluorine Chemistry, 2015, vol. 179, p. 175 - 178
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  • [ 108-98-5 ]
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Reference: [1] European Journal of Organic Chemistry, 2012, # 30, p. 5943 - 5952,10
[2] European Journal of Organic Chemistry, 2012, # 30, p. 5943 - 5952
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Reference: [1] European Journal of Organic Chemistry, 2012, # 30, p. 5943 - 5952,10
[2] European Journal of Organic Chemistry, 2012, # 30, p. 5943 - 5952
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 4, p. 703 - 708
[2] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 4, p. 703 - 708
[3] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 4, p. 703 - 708
[4] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 4, p. 703 - 708
[5] Chemistry Letters, 1995, # 7, p. 581 - 582
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Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 5, p. 396 - 400
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Reference: [1] Journal of Fluorine Chemistry, 1989, vol. 43, p. 53 - 66
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Reference: [1] Chinese Journal of Chemistry, 2018, vol. 36, # 3, p. 206 - 212
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Reference: [1] Journal of Fluorine Chemistry, 1989, vol. 43, p. 53 - 66
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YieldReaction ConditionsOperation in experiment
92%
Stage #1: With potassium <i>tert</i>-butylate; iodine In DMF (N,N-dimethyl-formamide) at -30 - -20℃; for 1 h;
Stage #2: With hydrogenchloride In water at -50℃;
Under an argon atmosphere, into a Schlenk flask containing difluoromethyl phenyl sulfone (192 mg, 1 mmol) and elemental iodine (508 mg, 4 mmol) in DMF (4 mL) at - 30 °C, was added dropwise via a syringe t-BuOK (448 mg, 4 mmol) in DMF (4 mL). The reaction mixture was stirred at - 30 - - 20 °C for 1 h, and the completion of the reaction was monitored by 19F NMR. The reaction was then quenched by adding IN HCI aqueous solution (5 mL) at - 50 °C, followed by warming to room temperature. A saturated NaCl aqueous solution (10 mL) was added, and the mixture was extracted with Et20 (15 mL x 3). The combined organic phase was dried over MgS04, filtered, and the solvent was removed in a rotary evaporator. The residue was further purified by silica gel column chromatography (hexane: ethyl acetate = 9: 1) to give difluoroiodomethyl phenyl sulfone (5) (294 mg, 92 percent yield) as a colorless solid, which readily turns to red under light. 'H NMR (500 MHz, CDC13): 6 7.63 (t, J = 7.4 Hz, 2H) ; 7.79 (t, J = 7.4 Hz, 1H) ; 7.99 (d, J = 7.5 Hz, 2H). 13C NMR (125 MHz, CDC13): 6 102.5 (t, J = 355 Hz) ; 128.1; 129.7; 131.3; 136.1.19F NMR (470 MHz, CDC13): 6 - 52.2. MS (EI, m/z): 318 (M(at); 177; 142; 127. HRMS (El): m/z calcd for C7H5F2IO2S (M+) 317.9023, found 317.9013.
92% With iodine(I) bromide; potassium hydroxide In tetrachloromethane at 20 - 60℃; for 4 h; General procedure: To a solution of proper sulfone1 (10.0 mmol) in dry CCl4 (40 mL) powdered KOH (2.0 g,35.7 mmol) was added. The mixture was stirred and IBr (2.2 g, 10.6 mmol) in dry CCl4 (30mL) was added dropwise while maintaining the temperature of the mixture below 20 °C. Theresulting mixture was stirred for 2 h at room temperature, then for 2 h at 60 °C. After coolingto room temperature the precipitate of inorganic salts was filtered off and the filtrate wasevaporated to dryness under reduced pressure. The residue was crystallized from propan-2-ol.For the synthesis of the sulfone 5 amount of IBr and KOH was increased twice.
Reference: [1] Organic Letters, 2004, vol. 6, # 23, p. 4315 - 4317
[2] Patent: WO2005/97739, 2005, A2, . Location in patent: Page/Page column 9; 17
[3] Tetrahedron Letters, 2014, vol. 55, # 3, p. 745 - 748
[4] Patent: WO2005/97739, 2005, A2, . Location in patent: Page/Page column 9
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