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[ CAS No. 120120-26-5 ] {[proInfo.proName]}

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Chemical Structure| 120120-26-5
Chemical Structure| 120120-26-5
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Product Details of [ 120120-26-5 ]

CAS No. :120120-26-5 MDL No. :MFCD00192520
Formula : C7H15F3Si Boiling Point : -
Linear Structure Formula :- InChI Key :ZHSKFONQCREGOG-UHFFFAOYSA-N
M.W : 184.27 Pubchem ID :4204914
Synonyms :

Safety of [ 120120-26-5 ]

Signal Word:Danger Class:3
Precautionary Statements:P210 UN#:1993
Hazard Statements:H225 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 120120-26-5 ]

* 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 [ 120120-26-5 ]

[ 120120-26-5 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 615-37-2 ]
  • [ 120120-26-5 ]
  • [ 13630-19-8 ]
  • 2
  • [ 637-87-6 ]
  • [ 120120-26-5 ]
  • [ 98-56-6 ]
YieldReaction ConditionsOperation in experiment
35 <unit not given> With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 24h;
63 %Spectr. With potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide at 20 - 60℃; Inert atmosphere;
  • 3
  • [ 75-63-8 ]
  • [ 994-30-9 ]
  • [ 120120-26-5 ]
YieldReaction ConditionsOperation in experiment
69% With hexaethylphosphoric triamide In dichloromethane at -78℃; for 2h;
  • 4
  • [ 13329-40-3 ]
  • [ 120120-26-5 ]
  • [ 709-63-7 ]
  • [ 783-79-9 ]
  • [ 133512-61-5 ]
YieldReaction ConditionsOperation in experiment
1: 17 (unit not given) 2: 6 (unit not given) 3: 45 <unit not given> With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 24h;
1: 45 (unit not given) 2: 17 (unit not given) 3: 6 <unit not given> With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 24h;
1: 45 (unit not given) 2: 6 (unit not given) 3: 17 <unit not given> With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 24h;
  • 5
  • [ 625-95-6 ]
  • [ 120120-26-5 ]
  • [ 401-79-6 ]
YieldReaction ConditionsOperation in experiment
78 <unit not given> With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 24h;
  • 6
  • [ 624-31-7 ]
  • [ 120120-26-5 ]
  • [ 6140-17-6 ]
  • 7
  • [ 66291-51-8 ]
  • [ 120120-26-5 ]
  • [ 133512-62-6 ]
YieldReaction ConditionsOperation in experiment
90 <unit not given> With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 24h;
  • 8
  • [ 612-55-5 ]
  • [ 120120-26-5 ]
  • [ 581-90-8 ]
YieldReaction ConditionsOperation in experiment
94 <unit not given> With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 24h;
  • 9
  • [ 696-62-8 ]
  • [ 120120-26-5 ]
  • [ 402-52-8 ]
  • [ 14038-06-3 ]
  • 10
  • [ 719-22-2 ]
  • [ 120120-26-5 ]
  • [ 120120-30-1 ]
YieldReaction ConditionsOperation in experiment
70% With potassium fluoride In acetonitrile for 1h; Ambient temperature;
41% With potassium carbonate In N,N-dimethyl-formamide XI 2,6-Di-tert-butyl-4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one EXAMPLE XI 2,6-Di-tert-butyl-4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one The procedure of Example V was repeated using a mixture of 176 mg (0.80 mmol) of 2,6-di-tert-butyl-1,4-benzoquinone, 147 mg (0.80 mmol) of triethyltrifluoromethylsilane, 22 mg (0.16 mmol) of potassium carbonate, and 1 mL of N,N-dimethylformamide at 25° C. for 21.5 hours. PTLC afforded 133 mg (41% yield) of 2,6-di-tert -butyl-4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one as a colorless liquid: 1 H NMR (CDCl3) δ 0.39-1.10 (m, 15H), 1.22 (s, 18H), 650 (s, 2H); 19 F NMR (CDCl3, relative to CFCl3) -80.5 ppm (s); IR (neat) 2957, 2910, 2876, 1670, 1648, 1457, 1364, 1333, 1272, 1255, 1178, 1151, 1070, 1033, 994, 880, 845, 747 cm-1; mass spectrum (70 eV) m/z (relative intensity 375 (60, M-C2 H5), 335 (50), 299 (20), 57 (100) 41 (40). Anal. Calcd. for C21 H35 F3 O2 Si: C, 62.34; H, 8.72. Found: C, 63.05; H, 8.75.
41% With potassium carbonate In N,N-dimethyl-formamide IX 2,6-Di-tert-butyl-4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one EXAMPLE IX 2,6-Di-tert-butyl-4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one The procedure of Example III was repeated using a mixture of 176 mg (0.80 mmol) of 2,6-di-tert-butyl-1,4-benzoquinone, 147 mg (0.80 mmol) of triethyltrifluoromethylsilane, 22 mg (0.16 mmol) of potassium carbonate, and 1 mL of N,N-dimethylformamide at 25° C. for 21.5 hours. PTLC afforded 133 mg (41% yield) of 2,6-di-tert-butyl-4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one as a colorless liquid: 1 H NMR (CDCl3)δ0.39-1.10 (m, 15H), 1.22 (s, 18H), 6.50(s, 2H); 19 F NMR (CDCl3, relative to CFCl3) -80.5 ppm (s); IR (neat) 2957, 2910, 2876, 1670, 1648, 1457, 1364, 1333, 1272, 1255, 1178, 1151, 1070, 1033, 994, 880, 845, 747 cm-1; mass spectrum (70 eV) m/z (relative intensity) 375 (60, M-C2 H5), 335 (50), 299 (20), 57 (100) 41 (40). Anal. Calcd. for C21 H35 F3 O2 Si: C, 62.34; H, 8.72. Found: C, 63.05; H, 8.75.
  • 11
  • [ 103-64-0 ]
  • [ 120120-26-5 ]
  • [ 55009-95-5 ]
  • (E)-3,3,3-trifluoro-1-phenylpropene [ No CAS ]
  • [ 74031-42-8 ]
YieldReaction ConditionsOperation in experiment
14% With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 24h; Yields of byproduct given;
14 (unit not given) With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 24h; Yield given;
  • 12
  • [ 3383-21-9 ]
  • [ 120120-26-5 ]
  • [ 120120-31-2 ]
YieldReaction ConditionsOperation in experiment
90% With potassium fluoride In acetonitrile for 1h; Ambient temperature;
83% With potassium carbonate In acetonitrile XII 4,6-Di-tert-butyl-2-triethylsiloxy-2-trifluoromethyl-3,5-cyclohexadien-1-one EXAMPLE XII 4,6-Di-tert-butyl-2-triethylsiloxy-2-trifluoromethyl-3,5-cyclohexadien-1-one The procedure of Example V was repeated using a mixture of 176 mg (0.80 mmol) of 3,5-di-tert-butyl-1,2-benzoquinone, 147 mg (0.80 mmol) of triethyltrifluoromethylsilane, 22 mg (0.16 mmol) of potassium carbonate, and 1 mL of acetonitrile at 25 C for 24 hours. PTLC afforded 269 mg (83% yield) of 4,6-di-tert -butyl-2-triethylsiloxy-2-trifluoromethyl-3,5-cyclohexadien-1-one as a yellow liquid: 1 H NMR (CDCl3) δ 0.35-1.10 (m, 15H), 1.16 (s, 3H), 1.23 (s, 3H), 5.85 (d, 1H, J=2 Hz), 6.84 (d, 1H, J=2 Hz); 19 F NMR (CDCl3, relative to CFCl3) -80.0 ppm (s); IR (neat) 2955, 2909, 2874, 1689, 1459, 1366, 1270, 1244, 1179, 1143, 1072, 1033, 998, 890, 831, 810, 743, 695 cm-1; mass spectrum (70 eV) m/z (relative intensity) 404 (29, M+), 389 (20), 375 (79, M-C2 H5), 57 (100).
83% With potassium carbonate In acetonitrile X 4,6-Di-tert-butyl-2-Triethylsiloxy-2-trifluoromethyl-3,5-cyclohexadien-1-one EXAMPLE X 4,6-Di-tert-butyl-2-Triethylsiloxy-2-trifluoromethyl-3,5-cyclohexadien-1-one The procedure of Example III was repeated using a mixture of 176 mg (0.80 mmol) of 3,5-di-tert-butyl-1,2-benzoquinone, 147 mg (0.80 mmol) of triethyltrifluoromethylsilane, 22 mg (0.16 mmol) of potassium carbonate, and 1 mL of acetonitrile at 25° C. for 24 hours. PTLC afforded 269 mg (83% yield) of 4,6-di-tert-butyl-2-triethylsiloxy-2-trifluoromethyl-3,5-cyclohexadien-1-one as a yellow liquid: 1 H NMR (CDCl3)δ0.35-1.10 (m, 15H), 1.16 (s, 3H), 1.23 (s, 3H), 5.85 (d, 1H, J =2 Hz), 6.84 (d, 1H, J=2 Hz); 19 F NMR (CDCl3, relative to CFCl3) -80.0 ppm (s); IR (neat) 2955, 2909, 2874, 1689, 1459, 1366, 1270, 1244, 1179, 1143, 1072, 1033, 998, 890, 831, 810, 743, 695 cm-1; mass spectrum (70 eV) m/z (relative intensity) 404 (29, M+), 389 (20), 375 (79, M-C2 H5), 57 (100). Anal. Calcd. for C21 H35 F3 O2 Si: C, 62.34; H, 8.72. Found: C, 62.46; H, 8.69.
  • 13
  • [ 51934-41-9 ]
  • [ 120120-26-5 ]
  • [ 583-02-8 ]
  • [ 133512-60-4 ]
  • 14
  • [ 100-39-0 ]
  • [ 120120-26-5 ]
  • [ 21249-93-4 ]
YieldReaction ConditionsOperation in experiment
73 <unit not given> With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 24h;
  • 15
  • [ 84-65-1 ]
  • [ 120120-26-5 ]
  • [ 120120-33-4 ]
YieldReaction ConditionsOperation in experiment
86% With potassium fluoride In N,N-dimethyl-formamide for 1h; Ambient temperature;
82% With potassium carbonate In N,N-dimethyl-formamide XIV 9,10-Dihydro-9-oxo-10-triethylsiloxy-10-trifluoromethylanthracene EXAMPLE XIV 9,10-Dihydro-9-oxo-10-triethylsiloxy-10-trifluoromethylanthracene The procedure of Example X was repeated using a mixture of 167 mg (0.80 mmol) of 9,10-anthraquinone, 147 mg (0.80 mmol) of triethyltrifluoromethylsilane, 22 mg (0.16 mmol) of potassium carbonate, and 2 mL of N,N-dimethylformamide at 25.C for 5 hours. PTLC afforded 258 mg (82% yield) of 9,10-dihydro-9-oxo-10-tri -ethylsiloxy-10-trifluoromethylanthracene as a colorless liquid: 1 H NMR (CDCl3) δ 0.19-0.90 (m, 15H), 7.50-7.90 (m, 4H), 7.90-8.13 (m, 2H), 8.30-8.47 (m, 2H); 19 F NMR (CDCl3, relative to CFCl3) -79.9 ppm (s) (t, JFH =14 Hz); IR (neat) 2959, 2931, 2875, 1667, 1589, 1455, 1412, 1320, 1272, 1245, 1179, 1134, 1087, 1012, 959, 932, 893, 841, 817, 763, 736, 715, 692, 662, 630, 596 cm-1; mass spectrum (70 eV) m/z (relative intensity) 363 (10, M-C2 H5), 211 (100), 183 (25), 77 (35). Anal. Calcd. for C21 H23 F3 O2 Si: C, 64.26; H, 5.91. Found: C, 64.26; H, 6.01.
  • 16
  • [ 120120-26-5 ]
  • [ 4392-24-9 ]
  • [ 17531-34-9 ]
YieldReaction ConditionsOperation in experiment
23 <unit not given> With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 24h;
  • 17
  • [ 120120-26-5 ]
  • [ 84-11-7 ]
  • [ 120120-34-5 ]
YieldReaction ConditionsOperation in experiment
86% With potassium fluoride In N,N-dimethyl-formamide for 1h; Ambient temperature;
83% With potassium carbonate In N,N-dimethyl-formamide XV 9,10-Dihydro-9-oxo-10-triethylsiloxy-10-trifluoromethylphenanthrene EXAMPLE XV 9,10-Dihydro-9-oxo-10-triethylsiloxy-10-trifluoromethylphenanthrene The procedure of Example X was repeated using a mixture of 167 mg (0.80 mmol) of 9,10-phenanthrenequinone, 147 mg (0.80 mmol) of triethyltrifluoromethylsilane, 22 mg (0.16 mmol) of potassium carbonate, and 2 mL of N,N-dimethylformamide at 25 C for 4 hours. PTLC afforded 260 mg (83% yield) of 9,10-dihydro-9-oxo -10-triethylsiloxy-10-trifluoromethylphenanthrene as a pale yellow liquid: 1 H NMR (CDCl3) δ 0.45-1.17 (m, 15H), 7.31-8.10 (m, 8H); 19 F NMR (CDCl3, relative to CFCl3) -79.4 ppm (s); IR (neat) 2953, 2909, 2874, 1707, 1598, 1450, 1298, 1279, 1251, 1230, 1178, 1117, 1029, 1009, 944, 918, 837, 778, 766, 757, 731, 630 cm-1; mass spectrum (70 eV) m/z (relative intensity) 363 (49, M-C2 H5), 294 (100), 236 (29). Anal. Calcd. for C21 H23 F3 O2 Si: C, 64.26; H, 5.91. Found: C, 64.28; H, 5.92.
83% With potassium carbonate In N,N-dimethyl-formamide XIII 9,10-Dihydro-9-oxo-10-triethylsiloxy-10-trifluoromethylphenanthrene EXAMPLE XIII 9,10-Dihydro-9-oxo-10-triethylsiloxy-10-trifluoromethylphenanthrene The procedure of Example VIII was repeated using a mixture of 167 mg (0.80 mmol) of 9,10-phenanthrenequinone, 147 mg (0.80 mmol) of triethyltrifluoromethylsilane, 22 mg (0.16 mmol) of potassium carbonate, and 2 mL of N,N-dimethylformamide at 25° C. for 4 hours. PTLC afforded 260 mg (83% yield) of 9,10-dihydro-9-oxo-10-triethylsiloxy-10-trifluoromethylphenanthrene as a pale yellow liquid: 1 H NMR (CDCl3) δ 0.45-1.17 (m, 15H), 7.31-8.10 (m, 8H); 19 F NMR (CDCl3, relative to CFCl3) -79.4 ppm (s); IR (neat) 2953, 2909, 2874, 1707, 1598, 1450, 1298, 1279, 1251, 1230, 1178, 1117, 1029, 1009, 944, 918, 837, 778, 766, 757, 731, 630 cm-1; mass spectrum (70 eV) m/z (relative intensity) 363 (49, M-C2 H5), 294 (100), 236 (29). Anal. Calcd. for C21 H 23 F3 O2 Si: C, 64.26; H, 5.91. Found: C, 64.28; H, 5.92.
  • 18
  • [ 120120-26-5 ]
  • [ 106-51-4 ]
  • [ 120120-28-7 ]
YieldReaction ConditionsOperation in experiment
72% With potassium fluoride In acetonitrile for 1h; Ambient temperature;
53% With potassium carbonate In N,N-dimethyl-formamide VIII 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one EXAMPLE VIII 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one The procedure of Example VI was repeated using a mixture of 86 mg (0.80 mmol) of 1,4-benzoquinone, 147 mg (0.80 mmol) of triethyltrifluoromethylsilane, 22 mg (0.16 mmol) of potassium carbonate, and 1 mL of N,N-dimethylformamide at 25° C. for 1 hour. Extraction of the aqueous mixture with diethyl ether and PTLC afforded 123 mg (53% yield) of 4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one.
51% With potassium carbonate In acetonitrile IX 4Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one EXAMPLE IX 4Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one The procedure of Example V was repeated using a mixture of 86 mg (0.80 mmol) of 1,4-benzoquinone, 147 mg (0.80 mmol) of triethyltrifluoromethylsilane, 22 mg (0.16 mmol) of potassium carbonate, and 1 mL of acetonitrile at 25.C for 7 hours. PTLC afforded 120 mg (51% yield) of 4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one.
51% With potassium carbonate In acetonitrile VII 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one EXAMPLE VII 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one The procedure of Example III was repeated using a mixture of 86 mg (0.80 mmol) of 1,4-benzoquinone, 147 mg (0.80 mmol) of triethyltrifluoromethylsilane, 22 mg (0.16 mmol) of potassium carbonate, and 1 mL of acetonitrile at 25° C. for 7 hours. PTLC afforded 120 mg (51% yield) of 4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one.
50% With dmap In acetonitrile XIX 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one EXAMPLE XIX 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one A mixture of 86 mg (0.80 mmol) of 1,4-benzoquinone, 147 mg (0.80 mmol) of triethyltrifluoromethylsilane, 5 mg (0.04 mmol) of 4-dimethylaminopyridine, and 1 mL of acetonitrile was stirred at 25° C. overnight and concentrated in vacuo. The resulting residue was purified by preparative thin layer chromatography (one 2 mm silica gel plate eluted with 50% dichloromethane-50% petroleum ether), to give 116 mg (50% yield) of 4-triethylsiloxy -4-trifluoromethyl-2,5-cyclohexadien-1-one as an amber liquid: 1 H NMR (CDCl3) δ 0.40-1.06 (m, 15H), 6.41 (d, 2H, J=9 Hz), 6.89 (d, 2H, J=9 Hz); 19 F NMR (CDCl3, relative to CFCl3) -83.8 ppm (t, JFH =4 Hz); IR (neat) 2956, 2912, 2877, 1677, 1611, 1265, 1240, 1182, 1129, 1067, 1004, 835, 749, 732 cm-1; mass spectrum (70 eV) m/z (relative intensity) 263 (6, M-C2 H5), 139 (79), 111 (100), 105 (68), 83 (41), 83 (41), 77 (100), 47 (31), 45 (35). Anal. Calcd. for C13 H19 F3 O2 Si: C, 53.39; H, 6.54. Found: C, 53.60; H, 6.79.
43% With hydrogenchloride In acetonitrile VIII 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one EXAMPLE VIII 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one A mixture of 83 mg (0.77 mmol) of 1,4-benzoquinone, 166 mg (0.90 mmol) of triethyltrifluoromethylsilane, 113 mg (2.3 mmol) of ground lithium azide, and 1 mL of acetonitrile was stirred at 25° C. for 22 hours. The reaction mixture was poured into 20 mL of 1N HCl and the resulting aqueous mixture was extracted with three 10 mL portions of dichloromethane. Combination, drying (MgSO4), and concentration of the organic layers afforded a residue which was purified by PTLC, giving 96 mg (43% yield) of 4-triethyl -siloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one.
43% With hydrogenchloride In acetonitrile VI 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one EXAMPLE VI 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one A mixture of 83 mg (0.77 mmol) of 1,4-benzoquinone, 166 mg (0.90 mmol) of triethyltrifluoromethylsilane, 113 mg (2.3 mmol) of ground lithium azide, and 1 mL of acetonitrile was stirred at 25° C. for 22 hours. The reaction mixture was poured into 20 mL of 1N HCl and the resulting aqueous mixture was extracted with three 10 mL portions of dichloromethane. Combination, drying (MgSO4), and concentration of the organic layers afforded a residue which was purified by PTLC, giving 96 mg (43% yield) of 4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one.
41% In acetonitrile V 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one EXAMPLE V 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one A mixture of 165 mg (1.5 mmol) of 1,4-benzoquinone, 332 mg (18 mmol) of triethyltrifluoromethylsilane, 15 mg (0.31mmol) of sodium cyanide, and 2 mL of acetonitrile was stirred vigorously at 25° C. for 42 hours. The mixture was filtered and the filtrate was concentrated in vacuo. Purification of the resulting residue by preparative thin layer chromatography (one 2 mm silica gel plate eluted with 50% dichloromethane - 50% petroleum ether) afforded 178 mg (41% yield) of 4-triethylsiloxy-4-trifluoromethyl -2,5-cyclohexadien-1-one as a pale yellow liquid: bp 68-78° C. at 0.5 torr; 1 H NMR (CDCl3) δ 0.40-1.06 (m, 15H), 6.41 (d, 2H, J=9 Hz), 6.89 (d, 2H, J=9 Hz); 19 F NMR (CDCl3, relative to CFCl3) -83.8 ppm (t, JFH =4 Hz); IR (neat) 2956, 2912, 2877, 1677, 1611, 12.65, 12.40, 1182, 1129, 1067, 1004, 835, 749, 732 cm-1; mass spectrum (70 eV) m/z (relative intensity) 263 (6, M-C2 H5), 139 (79), 111 (100) 105 (68), 83 (41), 77 (100), 47 (31), 45 (35). Anal. Calcd. for C13 H19 F3 O2 Si: C, 53.39; H, 6.54. Found: C, 53.60; H, 6.79.
41% In acetonitrile III 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one EXAMPLE III 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one A mixture of 165 mg (1.5 mmol) of 1,4-benzoquinone, 332 mg (18 mmol) of triethyltrifluoromethylsilane, 15 mg (0.31 mmol) of sodium cyanide, and 2 mL of acetonitrile was stirred vigorously at 25° C. for 42 hours. The mixture was filtered and the filtrate was concentrated in vacuo. Purification of the resulting residue by preparative thin layer chromatography (one 2 mm silica gel plate eluted with 50% dichloromethane - 50% petroleum ether) afforded 178 mg (41% yield) of 4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one as a pale yellow liquid: bp 68°-78° C. at 0.5 torr; 1 H NMR (CDCl3)δ0.40-1.06 (m, 15H), 6.41 (d, 2H, J =9 Hz), 6.89 (d, 2H, J =9 Hz); 19 F NMR (CDCl3, relative to CFCl3) -83.8 ppm (t, JFH =4 Hz); IR (neat) 2956, 2912, 2877, 1677, 1611, 12.65, 12.40, 1182, 1129, 1067, 1004, 835, 749, 732 cm-1; mass spectrum (70 eV) m/z (relative intensity) 263 (6, M-C2 H5), 139 (79), 111 (100) 105 (68), 83 (41), 77 (100), 47 (31), 45 (35). Anal. Calcd. for C13 H19 F3 O2 Si: C, 53.39; H, 6.54. Found: C, 53.60; H, 6.79.
29% With sodium hydroxide In water; acetonitrile VII 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one EXAMPLE VII 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one A mixture of 83 mg (0.77 mmol) of 1,4-benzoquinone, 1.66 mg (0.90 mmol) of triethyltrifluoromethylsilane,92 mg (2.3 mmol) of powdered sodium hydroxide, and 1 mL of acetonitrile was stirred at 25° C. for 2 hours. The reaction mixture was poured into 20 mL of water and the resulting aqueous mixture was extracted with two 5 mL portions of dichloromethane. Combination, drying (MgSO4), and concentration of the organic layers afforded a residue which was purified by PTLC, giving 66 mg (29% yield) of 4-triethyl -siloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one.
29% With sodium hydroxide In water; acetonitrile V 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one EXAMPLE V 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one A mixture of 83 mg (0.77 mmol) of 1,4-benzoquinone, 1.66 mg (0.90 mmol) of triethyltrifluoromethylsilane, 92 mg (2.3 mmol) of powdered sodium hydroxide, and 1 mL of acetonitrile was stirred at 25° C. for 2 hours. The reaction mixture was poured into 20 mL of water and the resulting aqueous mixture was extracted with two 5 mL portions of dichloromethane. Combination, drying (MgSO4), and concentration of the organic layers afforded a residue which was purified by PTLC, giving 66 mg (29% yield) of 4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one.
With potassium fluoride In acetonitrile

  • 19
  • [ 120120-26-5 ]
  • [ 130-15-4 ]
  • [ 120120-32-3 ]
YieldReaction ConditionsOperation in experiment
44% With potassium fluoride In acetonitrile for 1h; Ambient temperature;
41% With potassium carbonate In N,N-dimethyl-formamide XIII 1,4-Dihydro-1-oxo-4-triethylsiloxy-4-trifluoromethylnaphthalene EXAMPLE XIII 1,4-Dihydro-1-oxo-4-triethylsiloxy-4-trifluoromethylnaphthalene The procedure of Example X was repeated using a mixture of 127 mg (0.80 mmol) of 1,4-naphthoquinone, 147 mg (0.80 mmol) of triethyltrifluoromethylsilane, 22 mg (0.16 mmol) of potassium carbonate, and 1 mL of N,N-dimethylformamide at 25 C for 2 hours. PTLC afforded 113 mg (41% yield) of 1,4-dihydro-1-oxo-4-triethyl -siloxy-4-trifluoromethylnaphthalene as a brown liquid: 1 H NMR (CDCl3) δ 0.30-1.00 (m, 15H), 6.65 (d, 1H, J=10 Hz), 7.06 (d, 1H, J=10 Hz), 7.50-8.30 (m, 4H); 19 F NMR (CDCl3, relative to CFCl3) -79.6 ppm (s); IR (neat) 2956, 2911, 2876, 1676, 1599, 1454, 1379, 1299, 1253, 1178, 1154, 1110, 1065, 1058, 1018, 952, 836, 767, 748, 732 cm-1; mass spectrum (70 eV) m/z (relative intensity) 313 (40, M-C2 H 5), 189 (55), 161 (100), 133 (55), 77 (30). Anal. Calcd. for C17 H21 F3 O2 Si: C, 59.62; H, 6.18. Found: C, 59.91; H, 6.33.
41% With potassium carbonate In N,N-dimethyl-formamide XI 1,4-Dihydro-1-oxo-4-triethylsiloxy-4-trifluoromethylnaphthalene EXAMPLE XI 1,4-Dihydro-1-oxo-4-triethylsiloxy-4-trifluoromethylnaphthalene The procedure of Example VIII was repeated using a mixture of 127 mg (0.80 mmol) of 1,4-naphthoquinone, 147 mg (0.80 mmol) of triethyltrifluoromethylsilane, 22 mg (0.16 mmol) of potassium carbonate, and 1 mL of N,N-dimethylformamide at 25° C. for 2 hours. PTLC afforded 113 mg (41% yield) of 1,4-dihydro-1-oxo-4-triethylsiloxy-4-trifluoromethylnaphthalene as a brown liquid: 1 H NMR (CDCl3)δ0.30-1.00 (m, 15H), 6.65 (d, 1H, J=10 Hz), 7.06 (d, 1H, J=10 Hz), 7.50-8.30 (m, 4 H); 19 F NMR (CDCl3, relative to CFCl3) -79.6 ppm (s); IR (neat) 2956, 2911, 2876, 1676, 1599, 1454, 1379, 1299, 1253, 1178, 1154, 1110, 1065, 1058, 1018, 952, 836, 767, 748, 732 cm-1; mass spectrum (70 eV) m/z (relative intensity) 313 (40, M-C 2 H5), 189 (55), 161 (100), 133 (55), 77 (30). Anal. Calcd. for C17 H21 F3 O2 Si: C, 59.62; H, 6.18. Found: C, 59.91; H, 6.33.
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;

  • 20
  • [ 120120-26-5 ]
  • [ 214344-15-7 ]
  • ((S)-1-Benzyl-3,3,3-trifluoro-2-triethylsilanyloxy-2-trifluoromethyl-propyl)-trityl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 0.5h;
  • 21
  • [ 120120-26-5 ]
  • [ 133886-40-5 ]
  • N-(2-propenyl)-N-[3-(triethylsilyl)-2-propynyl]tosylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With cesium fluoride In tetrahydrofuran at 20℃; for 2.5h;
  • 22
  • [ 994-30-9 ]
  • [ 426-58-4 ]
  • [ 120120-26-5 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: (trifluoromethylsulfonyl)benzene With magnesium In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: triethylsilyl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.3h;
With magnesium In N,N-dimethyl-formamide 2 Preparation of (trifluoromethyl)triethylsilane (15) Example 2 Preparation of (trifluoromethyl)triethylsilane (15) Into a flame-dried Schlenk flask containing 1.03 g (43 mmol) magnesium turnings and 30 mL DMF under argon, was added 3.0 g (14 mmol) of trifluoromethyl phenyl sulfone (1) at 0° C. After stirring for 5 minutes, 6.45 g (43 mmol) triethylsilyl chloride was added dropwise via syringe. The color of the reaction mixture slowly turned yellow. The progress of the reaction was monitored by 19F NMR periodically. After 1 h, the mixture was slowly warmed to room temperature over 20 minutes period and the reaction mixture was washed with 50 mL ice water. After removing the excess Mg, the solution was extracted with pentane (30 mL*3). The pentane phase was washed carefully with cold 98% sulfuric acid (30 mL*4) to remove most of the siloxane and silanol. Subsequently, the organic phase was washed with cold water (30 mL*2), saturated aqueous NaHCO3 solution (30 mL*2), water (20 mL*2) and dried over anhydrous magnesium sulfate. The solvent was removed under vacuum (~100 Torr), and the resulting crude product also contains PhSSPh as a byproduct (characterized by both GC-MS and NMR).
  • 23
  • [ 994-30-9 ]
  • [ 703-18-4 ]
  • [ 120120-26-5 ]
YieldReaction ConditionsOperation in experiment
98 % Spectr. With magnesium In N,N-dimethyl-formamide at 20℃; for 0.5h;
  • 24
  • [ 673475-55-3 ]
  • [ 120120-26-5 ]
  • [ 673475-57-5 ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; copper(l) iodide In DMF (N,N-dimethyl-formamide) at 80℃; for 72h; 107 PPEPARATIVE EXAMPLE 107 A mixture of the compound prepared in Preparative Example 102 (1.00 [MMOL),] triethyl [(TRIFLUOROMETHYL) SILANE] (3.60 [MMOL),] potassium fluoride (3.60 [MMOL),] and Cul (4.46 [MMOL)] in anhydrous DMF (4 mL) is stirred in a closed pressure vessel at [80°C] for 72 hr. [CH2CI2] (80 mL) is added and the mixture is filtered through Celite. The solvent is evaporated and the residue is purified by flash chromatography to give the desired product.
  • 25
  • [ 672324-51-5 ]
  • [ 120120-26-5 ]
  • [ 672326-04-4 ]
YieldReaction ConditionsOperation in experiment
15% With potassium fluoride; copper(l) iodide In DMF (N,N-dimethyl-formamide) at 80℃; for 72h; 427.A EXAMPLE 427; STEP A A mixture of the compound prepared in Preparative Example 194 (527 mg, 1.00 MMOL), triethyl (trifluoromethyl) silane (666 mg, 3.60 MMOL), potassium fluoride (210 mg, 3.60 MMOL), and Cul (850 mg, 4.46 MMOL) in anhydrous DMF (4 mL) was stirred in a closed pressure vessel at 80 C for 72 hr. CH2CI2 (80 mL) was added and the mixture was filtered through Celite. The solvent was evaporated and the residue was purified by flash chromatography using 2: 1 CH2CI2 : EtOAc as eluent to yield pale orange. waxy solid (70 mg, 15%). LCMS: M+=470.
  • 26
  • [ 75-09-2 ]
  • [ 120120-26-5 ]
  • [ 2283-11-6 ]
  • [ 106-51-4 ]
  • [ 120120-28-7 ]
YieldReaction ConditionsOperation in experiment
63% In water; acetonitrile XVII 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one EXAMPLE XVII 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one A mixture of 83 mg (0.77 mmol) of 1,4-benzoquinone, 1.66 mg (0.90 mmol) of triethyltrifluoromethylsilane, and 1 mL of acetonitrile was treated with one drop of hexaethylphosphorous triamide, stirred at 25 C for 23.5 hours, and poured into 20 mL of water. The resulting aqueous mixture was extracted with three 10 mL portions of dichloromethane. Combination, drying (MgSO4), and concentration of the organic layers afforded a residue which was purified by preparative thin layer chromatography (one 2 mm silica gel plate developed with 50% dichloromethan--50% petroleum ether), giving 142 mg (63% yield) of 4-triethylsiloxy -4-trifluoromethyl-2,5-cyclohexadien-1-one as an amber liquid: 1 H NMR (CDCl3) δ 0.40-1.06 (m, 15H), 6.41 (d, 2H, J=9 Hz), 6.89 (d, 2H, J=9 Hz); 19 F NMR (CDCl3, relative to CFCl3) -83.8 ppm (t, JFH =4 Hz); IR (neat) 2956, 2912, 2877, 1677, 1611, 1265, 1240, 1182, 1129, 1067, 1004, 835, 749, 732 cm-1; mass spectrum (70 eV) m/z (relative intensity) 263 (6, M-C2 H5), 139 (79), 111 (100), 105 (68), 83 (41), 77 (100), 47 (31), 45 (35).
  • 27
  • [ 120120-26-5 ]
  • [ 106-51-4 ]
  • [ 113281-23-5 ]
YieldReaction ConditionsOperation in experiment
42% In acetonitrile 4-Hydroxy-4-trifluoromethyl-2,5-cyclohexadien-1-one 4-Hydroxy-4-trifluoromethyl-2,5-cyclohexadien-1-one A mixture of 74 mg (1.3 mmol) of ground ammonium bifluoride (NH4 HF2), 119 mg (1.1 mmol) of 1,4-benzoquinone, and 2 mL of acetonitrile was treated with 239 mg (1.3 mmol) of triethyltrifluoromethylsilane and stirred vigorously at room temperature for 4 hours. The mixture was filtered and the filter cake was washed with dichloromethane. Concentration of the combined filtrates gave a black solid which was triturated with dichloromethane. The resulting mixture was filtered and the filter cake was washed with dichloromethane. Concentration of the combined filtrates afforded a brown solid which was purified by PTLC (one 2 mm silica gel plate eluted with a 2% methanol-98% dichloromethane) to give 83 mg (42% yield) of 4-hydroxy-4-tri -fluoromethyl-2,5-cyclohexadien-1-one.
  • 28
  • [ 1256935-40-6 ]
  • [ 120120-26-5 ]
  • [ 106-51-4 ]
  • [ 120120-28-7 ]
YieldReaction ConditionsOperation in experiment
41% In dichloromethane; acetonitrile IV 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one EXAMPLE IV 4-Triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one A mixture of 100 mg (1.3 mmol) of potassium bifluoride, 119 mg (1.1 mmol) of 1,4-benzoquinone, and 2 mL of acetonitrile was treated with 239 mg (1.3 mmol) of triethyltrifluoromethylsilane and stirred vigorously at room temperature for 2 hours. The mixture was filtered and the filter cake was washed with dichloromethane. Concentration of the combined filtrates gave a black oil which was dissolved in dichloromethane and loaded onto a column of silica gel. The column was washed with dichloromethane until the eluent contained no uV active material. Concentration of the eluent gave a colorless oil which was purified by PTLC (one 2 mm silica gel plate eluted with 50% dichloromethane-50% petroleum ether) to give 134 mg (41% yield) of 4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one.
  • 29
  • [ 146398-87-0 ]
  • [ 7681-65-4 ]
  • [ 120120-26-5 ]
  • [ 146398-88-1 ]
YieldReaction ConditionsOperation in experiment
With 1-methyl-pyrrolidin-2-one; potassium fluoride In N,N-dimethyl-formamide 11.iii Example 11 (iii) A mixture of 6-ethyl-4-iodo-2-methyl-1-phenylsulphonyl-1 H -pyrrolo[3,2- c ]pyridine (58O mg), copper (I) iodide (428 mg), potassium fluoride (1O4 mg) and triethyl(trifluoromethyl)silane (O.3 ml) in DMF (2 ml) and N-methylpyrrolidone (1.5 ml) was stirred and heated at 8O°C for 24 hours in a screw-capped reaction tube. The mixture was cooled, poured into water (5O ml) and extracted with ethyl acetate (3 x 2O ml). The combined extracts were washed with water (5 ml) and dried (MgSO4). The solvent was evaporated to give a gum (392 mg) which was purified by flash chromatography, eluding with a mixture of methanol and dichloromethane (1:99 v/v), to give 6-ethyl-2-methyl-1-phenylsulphonyl-4-trifluoromethyl-1 H -pyrrolo[3,2- c ]pyridine (21O mg); NMR (d6-DMSO): 1.29(t, 3H), 2.64(d, 3H), 2.95(q, 2H), 6.78(m, 1H), 7.59-7.87(m, 3H), 7.94-8.O5(m, 2H), 8.13(s, 1H); mass spectrum (+ve FAB, Methanol/NBA): 369 (M+H)+.
  • 30
  • [ 1057324-16-9 ]
  • [ 120120-26-5 ]
  • [ 1057324-17-0 ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 72h; 59 A mixture of the product from Preparative Example 58 (1.0 eq.), CF3SiEt3 (3.6 eq.), KF (3.6 eq.), and CuI (4.5 eq.) in DMF is stirred in a closed pressure vessel at 80° C. for 3 d. CH2Cl2 is added, the mixture is filtered through Celite, the solvent is evaporated, and the residue is chromatographed to yield the product.
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 72h; 59 A mixture of the product from Preparative Example 58 (1.0 eq.), CF3SiEt3 (3.6 eq.), KF (3.6 eq.), and CuI (4.5 eq.) in DMF is stirred in a closed pressure vessel at 80° C. for 3 d. CH2Cl2 is added, the mixture is filtered through Celite, the solvent is evaporated, and the residue is chromatographed to yield the product.
  • 31
  • [ 1030604-43-3 ]
  • [ 120120-26-5 ]
  • [ 1030604-44-4 ]
YieldReaction ConditionsOperation in experiment
50% With potassium fluoride In 1-methyl-pyrrolidin-2-one
  • 32
  • [ 16494-36-3 ]
  • [ 120120-26-5 ]
  • [ 256423-13-9 ]
  • 33
  • [ 69045-79-0 ]
  • [ 120120-26-5 ]
  • [ 52334-81-3 ]
YieldReaction ConditionsOperation in experiment
69 %Spectr. With potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide at 20 - 60℃; Inert atmosphere;
  • 34
  • [ 636-98-6 ]
  • [ 120120-26-5 ]
  • [ 402-54-0 ]
YieldReaction ConditionsOperation in experiment
70% With potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide at 20 - 60℃; Inert atmosphere;
  • 35
  • [ 6560-83-4 ]
  • [ 120120-26-5 ]
  • [ 347-42-2 ]
  • 36
  • [ 645-00-1 ]
  • [ 120120-26-5 ]
  • [ 98-46-4 ]
YieldReaction ConditionsOperation in experiment
63% With potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide at 20 - 60℃; Inert atmosphere;
  • 37
  • [ 3058-39-7 ]
  • [ 120120-26-5 ]
  • [ 455-18-5 ]
YieldReaction ConditionsOperation in experiment
80 %Spectr. With potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide at 20 - 60℃; Inert atmosphere;
  • 38
  • [ 51934-41-9 ]
  • [ 120120-26-5 ]
  • [ 583-02-8 ]
  • 39
  • [ 20651-67-6 ]
  • [ 120120-26-5 ]
  • [ 61342-04-9 ]
  • 40
  • [ 1206543-99-8 ]
  • [ 120120-26-5 ]
  • [ 1206813-37-7 ]
YieldReaction ConditionsOperation in experiment
3.5% With potassium fluoride In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide at 20 - 80℃; for 1.33333h; C.C.4 Step C.4: Preparation of the N-tert-butyl-2-[(3-chlorophenyl)aminol-5-(trifluoromethyl)-1 ,3-thiazole-4- carboxamide:N-tert-butyl^-KS-chlorophenylJaminol-δ-iodo-I .S-thiazole^-carboxamide (191 mg) is dissolved in DMF/NMP 1/1 (0.4 ml). Copper (I) iodide (114 mg) is added at room temperature. A solution of triethyl(trifluoromethyl)silane (2,226 g) and Potassium fluoride (695 mg) in DMF/NMP 1/1 (0,4 ml) is then added to the reaction mixture. After stirring for 20 minutes at 800C and 1 hour at room temperature, AcOEt is added and several washes with NaCI sat. are performed. The organic phase is concentrated and dried with MgSO4. The crude solid is purified by silica gel chromatography to give N- tert-butyl-2-[(3-chlorophenyl)amino]-5-(trifluoromethyl)-1 ,3-thiazole-4-carboxamide (yield: 3,5 %).
  • 41
  • [ 623-03-0 ]
  • [ 120120-26-5 ]
  • [ 455-18-5 ]
YieldReaction ConditionsOperation in experiment
72% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 130℃;
6 %Spectr. With potassium fluoride; bis(tri-t-butylphosphine)palladium(0) In 1,4-dioxane at 120℃; Inert atmosphere; Sealed tube;
  • 42
  • [ 5044-38-2 ]
  • [ 120120-26-5 ]
  • [ 92636-38-9 ]
YieldReaction ConditionsOperation in experiment
84% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 130℃;
  • 43
  • [ 26163-40-6 ]
  • [ 120120-26-5 ]
  • [ 411209-38-6 ]
YieldReaction ConditionsOperation in experiment
94% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(allyl)PdCl]2 In 1,4-dioxane at 120℃;
  • 44
  • [ 1240100-03-1 ]
  • [ 120120-26-5 ]
  • [ 1073968-22-5 ]
YieldReaction ConditionsOperation in experiment
76% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(allyl)PdCl]2 In 1,4-dioxane at 130℃;
  • 45
  • [ 941294-14-0 ]
  • [ 120120-26-5 ]
  • [ 1240100-16-6 ]
YieldReaction ConditionsOperation in experiment
72% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 130℃;
  • 46
  • [ 4521-05-5 ]
  • [ 120120-26-5 ]
  • [ 1240100-20-2 ]
YieldReaction ConditionsOperation in experiment
87% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 130℃;
  • 47
  • [ 60301-56-6 ]
  • [ 120120-26-5 ]
  • 2-phenyl-6-(trifluoromethyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(allyl)PdCl]2 In 1,4-dioxane at 130℃;
  • 48
  • [ 6265-91-4 ]
  • [ 120120-26-5 ]
  • [ 134384-31-9 ]
YieldReaction ConditionsOperation in experiment
90% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(allyl)PdCl]2 In 1,4-dioxane at 130℃;
  • 49
  • [ 15499-27-1 ]
  • [ 120120-26-5 ]
  • [ 61342-04-9 ]
YieldReaction ConditionsOperation in experiment
67% With potassium fluoride; dicyclohexyl[3,6-dimethoxy-2′,4′,6′-tris(1-methylethyl)[1,1′-biphenyl]-2-yl]phosphine; [(allyl)PdCl]2 In tetrahydrofuran at 110℃; for 20h;
65% With potassium fluoride at 130℃; for 20h; Glovebox;
84 %Chromat. With potassium fluoride; dicyclohexyl[3,6-dimethoxy-2′,4′,6′-tris(1-methylethyl)[1,1′-biphenyl]-2-yl]phosphine; Pd(π-allyl)(BrettPhos)Cl In 1,4-dioxane at 120℃; for 16h; 9 Example 9 (according to the invention) Trifluoromethanation Using fa-allyl)Pd(BrettPhos)CI In a nitrogen filled glovebox a 2 dram reaction vial equipped with a Teflon-coated magnetic stir bar is charged with (allyl)Pd(BrettPhos)CI (21 . 6 mg, 30 μηιοΙ), BrettPhos (16.1 mg, 30 μηιοΙ), and potassium fluoride (58.1 mg, 1 .0 mmol). Dioxane (1 .65 ml_), triethyl(trifluoromethyl)silane (188 μΙ_, 1 .0 mmol), and 1 -nbutyl-4-chlorobenzene (84.3 μΙ_, 0.50 mmol) are added via syringe. The reaction vial is capped with an open top cap and PTFE Faced Silicone septum, removed from the glovebox, and placed on a preheated aluminum block (120 °C) and stirred vigorously for 16 hours. After cooling to room temperature the vial is opened to air and an aliquot (~200 μΙ_) is removed, passed through a plug of Celite, eluted with ethyl acetate (2 ml_) and analyzed by GC. The benzotrifluoride product is observed in 84% GC yield (uncalibrated). This experiment demonstrates that the precatalyst (7i-allyl)Pd(BrettPhos)CI is competent in the trifluoromethanation of 4-n-butyl-1 -chlorobenzene.
  • 50
  • [ 716-53-0 ]
  • [ 120120-26-5 ]
  • [ 120568-02-7 ]
YieldReaction ConditionsOperation in experiment
90% With potassium fluoride; [(allyl)PdCl]2; ruphos In 1,4-dioxane at 140℃;
With potassium fluoride; bis(η3-allyl-μ-chloropalladium(II)); ruphos In 1,4-dioxane at 140℃; for 24h; Sealed tube;
  • 51
  • [ 39651-06-4 ]
  • [ 120120-26-5 ]
  • [ 959012-94-3 ]
YieldReaction ConditionsOperation in experiment
83% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(allyl)PdCl]2 In 1,4-dioxane at 120℃;
  • 52
  • [ 2403-61-4 ]
  • [ 120120-26-5 ]
  • [ 72360-67-9 ]
YieldReaction ConditionsOperation in experiment
72% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(allyl)PdCl]2 In 1,4-dioxane at 120℃;
  • 53
  • [ 5367-28-2 ]
  • [ 120120-26-5 ]
  • [ 67192-42-1 ]
YieldReaction ConditionsOperation in experiment
70% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(allyl)PdCl]2 In 1,4-dioxane at 130℃;
  • 54
  • [ 24318-02-3 ]
  • [ 120120-26-5 ]
  • [ 70097-64-2 ]
YieldReaction ConditionsOperation in experiment
88% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 130℃;
  • 55
  • [ 120120-26-5 ]
  • hexyl 4-chlorobenzoate [ No CAS ]
  • [ 959085-50-8 ]
YieldReaction ConditionsOperation in experiment
85 %Chromat. With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(allyl)PdCl]2 In 1,4-dioxane at 120℃;
  • 56
  • [ 120120-26-5 ]
  • [ 2051-62-9 ]
  • [ 398-36-7 ]
YieldReaction ConditionsOperation in experiment
84% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(allyl)PdCl]2 In 1,4-dioxane at 130℃;
58% With potassium fluoride at 130℃; for 20h; Glovebox;
  • 57
  • [ 120120-26-5 ]
  • 1-(3-chlorophenyl)piperidine [ No CAS ]
  • 1-(3-(trifluoromethyl)phenyl)piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 130℃;
  • 58
  • [ 120120-26-5 ]
  • [ 77801-60-6 ]
  • [ 1240100-19-9 ]
YieldReaction ConditionsOperation in experiment
80% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 130℃;
  • 59
  • [ 120120-26-5 ]
  • [ 90-13-1 ]
  • [ 26458-04-8 ]
YieldReaction ConditionsOperation in experiment
84% With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 130℃;
72% With potassium fluoride at 130℃; for 20h; Glovebox;
24 %Spectr. With potassium fluoride; bis(tri-t-butylphosphine)palladium(0) In 1,4-dioxane at 120℃; Inert atmosphere; Sealed tube;
With potassium fluoride; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 130℃; for 18h; Sealed tube;

  • 60
  • 1,2,3,6-tetrahydro-[1,1'-biphenyl]-4-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate [ No CAS ]
  • [ 120120-26-5 ]
  • [ 905567-11-5 ]
YieldReaction ConditionsOperation in experiment
71% With rubidium fluoride; bis(η3-allyl-μ-chloropalladium(II)); tert-butyl XPhos In 1,4-dioxane at 110℃; for 5h; Inert atmosphere;
  • 61
  • [ 1305205-57-5 ]
  • [ 120120-26-5 ]
  • [ 1346777-48-7 ]
YieldReaction ConditionsOperation in experiment
83% With rubidium fluoride; bis(η3-allyl-μ-chloropalladium(II)); tert-butyl XPhos In 1,4-dioxane at 90 - 110℃; Inert atmosphere;
  • 62
  • [ 1346777-14-7 ]
  • [ 120120-26-5 ]
  • [ 1346777-40-9 ]
YieldReaction ConditionsOperation in experiment
73% With rubidium fluoride; bis(η3-allyl-μ-chloropalladium(II)); tert-butyl XPhos In 1,4-dioxane at 110℃; for 5h; Inert atmosphere;
  • 63
  • [ 1346777-15-8 ]
  • [ 120120-26-5 ]
  • [ 1346777-41-0 ]
YieldReaction ConditionsOperation in experiment
51% With rubidium fluoride; bis(dibenzylideneacetone)-palladium(0); tert-butyl XPhos In 1,4-dioxane at 110℃; for 12h; Inert atmosphere;
  • 64
  • [ 1346777-20-5 ]
  • [ 120120-26-5 ]
  • [ 1346777-42-1 ]
YieldReaction ConditionsOperation in experiment
60% With rubidium fluoride; bis(dibenzylideneacetone)-palladium(0); tert-butyl XPhos In 1,4-dioxane at 110℃; for 12h; Inert atmosphere;
  • 65
  • [ 1346777-23-8 ]
  • [ 120120-26-5 ]
  • [ 1346777-44-3 ]
YieldReaction ConditionsOperation in experiment
76% With rubidium fluoride; bis(η3-allyl-μ-chloropalladium(II)); tert-butyl XPhos In 1,4-dioxane at 110℃; for 9h; Inert atmosphere;
  • 66
  • [ 1346777-30-7 ]
  • [ 120120-26-5 ]
  • [ 1346777-50-1 ]
YieldReaction ConditionsOperation in experiment
80% With rubidium fluoride; bis(η3-allyl-μ-chloropalladium(II)); tert-butyl XPhos In 1,4-dioxane at 90℃; for 10h; Inert atmosphere;
  • 67
  • [ 1346777-35-2 ]
  • [ 120120-26-5 ]
  • [ 1346777-52-3 ]
YieldReaction ConditionsOperation in experiment
90% With rubidium fluoride; bis(η3-allyl-μ-chloropalladium(II)); tert-butyl XPhos In 1,4-dioxane at 100℃; for 10h; Inert atmosphere;
  • 68
  • [ 75-46-7 ]
  • [ 994-30-9 ]
  • [ 120120-26-5 ]
YieldReaction ConditionsOperation in experiment
71% With potassium hexamethylsilazane In diethyl ether at -78 - 20℃;
71% Stage #1: trifluoromethan; triethylsilyl chloride In diethyl ether at -78℃; for 0.166667h; Inert atmosphere; Stage #2: With potassium hexamethylsilazane In diethyl ether at -78 - 20℃; for 3h; Inert atmosphere; 2 Preparation of Trifluoromethyl(triethyl)silane General procedure: Example 2 Preparation of Trifluoromethyl(triethyl)silane To a 250 ml round bottom flask with magnetic stirrer, under argon was added 140 ml of diethyl ether. This reaction flask was cooled to -78° C. using dry ice/acetone bath and was stirred at that temperature for ten minutes. After ten minutes, CF3H was bubbled into this ether solution for 16 min 17 sec (2.5 g was added total at the rate of 52.5 ml/min to obtain 0.25 M solution in ether). After 10 minutes, chlorotriethylsilane (5.32 g) was added to the reaction mixture dropwise and the resulting reaction mixture was stirred at -78° C. for ten minutes. After ten minutes, a solution of potassium hexamethyldisilazide in ether (7.4 g in 52 ml, 0.625 M solution in ether) was added dropwise to the reaction mixture and the resulting yellowish reaction mixture was stirred at -78° C. for 2 hours and then was gradually warmed to room temperature and stirred at room temperature for 1 hour. Ether was removed under vacuo and the residue obtained was dissolved in pentane (150 ml). Organic layer (pentane) layer was washed with water once (1*30 ml) and was further washed with cold concentrated sulfuric acid (98%) (4*15 ml) to remove most of the siloxane and silanols formed in the reaction. Organic layer was then washed with water (5*50 ml) until pH of the water showed neutral and dried over sodium sulfate. Solvent (pentane) was removed under vacuo to obtain crude product which was distilled under vacuo to obtain pure (trifluoromethyl)triethylsilane 4.6 g, 71% yield. 1H NMR (400 MHz): δ 0.79 (q, 3JH-H=7.9 Hz, 6H), 1.04 (t, 3JH-H=7.9 Hz, 9H), 13C NMR (100.5 MHz): δ 0.86 (s, CH2), 6.53 (s, CH3), 132.24 (q, 1JC-F=324 Hz, CF3), 19F NMR (376.3 MHz): δ-61.3 (s), 29Si NMR (79.5 MHz): δ 7.7 (q, 2JSi-F=32 Hz, 1 Si).
  • 69
  • [ 1379828-13-3 ]
  • [ 120120-26-5 ]
  • [ 871571-28-7 ]
YieldReaction ConditionsOperation in experiment
95 %Spectr. Stage #1: C14H20N4 With methyl iodide at 110℃; for 5h; Inert atmosphere; Stage #2: (trifluoromethyl)triethylsilane With potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In 1-methyl-pyrrolidin-2-one at 60℃; for 16h; Inert atmosphere;
  • 70
  • [ 122948-47-4 ]
  • [ 120120-26-5 ]
  • [ 905567-11-5 ]
  • [ 142273-41-4 ]
YieldReaction ConditionsOperation in experiment
1: 19% 2: 14% With potassium fluoride; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; tert-butyl XPhos In 2-methyltetrahydrofuran at 110℃; for 12h; Inert atmosphere; Glovebox; Sealed tube;
  • 71
  • C18H15F3O3 [ No CAS ]
  • [ 120120-26-5 ]
  • C19H16F6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
7.8% With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; for 10h; Inert atmosphere; 3 Synthesis of Compound (1-1-16) In a nitrogen atmosphere, the compound (T-5) (0.3 g, 0.89 mmol) obtained in the third step of Synthesis Example 1 and THF (30 ml) were placed in a reactor and cooled with ice. Trifluoromethyltriethylsilane (0.13 g, 0.94 mmol) and tetrabutylammonium fluoride (TBAF, 1.0 M; THF solution; 20 μl, 0.02 mmol) were added to a temperature range of 0 ° C. to -10 ° C. , And the mixture was stirred at room temperature for 10 hours. The reaction mixture was poured into water (30 ml) and extracted with ethyl acetate. The combined organic layers were washed with water and saturated brine in this order, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (heptane / ethyl acetate = 2/1, volume ratio) to give compound (1-1-16) (3.0 mg, 0.007 mmol; 7.8%) was obtained.
  • 72
  • C18H15F3O3 [ No CAS ]
  • [ 120120-26-5 ]
  • C19H16F6O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrabutyl ammonium fluoride In tetrahydrofuran at -10 - 20℃; for 10h; Inert atmosphere; Cooling with ice; 2.1 In a nitrogen atmosphere, the compound (1-1-2) (0.3 g, 0.89 mmol) obtained in the third step of Synthesis Example 1 and THF (30 ml) were placed in a reactor and cooled with ice. Thereto, trifluoromethyltriethylsilane (0.13 g, 0.94 mmol) and tetrabutylammonium fluoride (TBAF, 1.0 M; THF solution; 20 μl, 0.02 mmol) Was dropped in a temperature range of 0 ° C. to -10 ° C., And the mixture was stirred at room temperature for 10 hours. The reaction mixture was poured into water (30 ml) and extracted with ethyl acetate. The combined organic layers were washed with water and saturated brine in this order, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure to give compound (T-5). The compound (T-5) was not purified and used in the next reaction.
  • 73
  • [ 1126-46-1 ]
  • [ 120120-26-5 ]
  • [ 2967-66-0 ]
YieldReaction ConditionsOperation in experiment
55% With potassium fluoride at 130℃; for 20h; Glovebox;
  • 74
  • [ 120120-26-5 ]
  • [ 98-56-6 ]
  • [ 433-19-2 ]
  • 75
  • [ 29921-41-3 ]
  • [ 120120-26-5 ]
  • [ 7552-71-8 ]
YieldReaction ConditionsOperation in experiment
62% With potassium fluoride at 130℃; for 20h; Glovebox;
  • 76
  • [ 623-12-1 ]
  • [ 120120-26-5 ]
  • [ 402-52-8 ]
  • 77
  • [ 90-11-9 ]
  • [ 120120-26-5 ]
  • [ 26458-04-8 ]
YieldReaction ConditionsOperation in experiment
11 %Spectr. With potassium fluoride; bis(tri-t-butylphosphine)palladium(0) In 1,4-dioxane at 120℃; Inert atmosphere; Sealed tube;
  • 78
  • [ 95-49-8 ]
  • [ 120120-26-5 ]
  • [ 13630-19-8 ]
  • 79
  • [ 7335-27-5 ]
  • [ 120120-26-5 ]
  • [ 583-02-8 ]
  • 80
  • [ 95-46-5 ]
  • [ 120120-26-5 ]
  • [ 13630-19-8 ]
  • 81
  • [ 120120-26-5 ]
  • [ 95-15-8 ]
  • benzo[b]thiophen-2-yl triethylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With cesium fluoride at 0℃; for 24h; Glovebox;
  • 82
  • [ 2060-63-1 ]
  • [ 120120-26-5 ]
  • 5-carbonitrile-2-triethylsilylbenzo[b]thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With rubidium fluoride at 0℃; for 2h; Glovebox;
  • 83
  • [ 37847-52-2 ]
  • [ 120120-26-5 ]
  • 2,4-difluoro-3-triethylsilylbiphenyl [ No CAS ]
  • 84
  • [ 2714-87-6 ]
  • [ 120120-26-5 ]
  • [ 398-36-7 ]
YieldReaction ConditionsOperation in experiment
40% With potassium phosphate; [PdCl(cinnamyl)]2; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 170℃; for 16h;
37 mg With potassium phosphate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 170℃; for 16h; Inert atmosphere; Sealed tube;
  • 85
  • [1,1′-biphenyl]-2-carbonyl fluoride [ No CAS ]
  • [ 120120-26-5 ]
  • [ 362-59-4 ]
YieldReaction ConditionsOperation in experiment
71% With potassium phosphate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 170℃; for 16h; Inert atmosphere; Sealed tube;
Same Skeleton Products
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