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[ CAS No. 402-43-7 ] {[proInfo.proName]}

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Chemical Structure| 402-43-7
Chemical Structure| 402-43-7
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Product Details of [ 402-43-7 ]

CAS No. :402-43-7 MDL No. :MFCD00000398
Formula : C7H4BrF3 Boiling Point : -
Linear Structure Formula :- InChI Key :XLQSXGGDTHANLN-UHFFFAOYSA-N
M.W :225.01 Pubchem ID :67872
Synonyms :

Calculated chemistry of [ 402-43-7 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.14
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.26
Log Po/w (XLOGP3) : 3.76
Log Po/w (WLOGP) : 4.62
Log Po/w (MLOGP) : 4.1
Log Po/w (SILICOS-IT) : 3.51
Consensus Log Po/w : 3.65

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.94
Solubility : 0.0257 mg/ml ; 0.000114 mol/l
Class : Soluble
Log S (Ali) : -3.45
Solubility : 0.0793 mg/ml ; 0.000352 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.14
Solubility : 0.0162 mg/ml ; 0.0000719 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.16

Safety of [ 402-43-7 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P233-P240-P241-P242-P243-P264-P280-P303+P361+P353-P305+P351+P338-P332+P313-P337+P313-P370+P378-P403+P235-P501 UN#:1993
Hazard Statements:H225-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 402-43-7 ]

* 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.

  • Upstream synthesis route of [ 402-43-7 ]
  • Downstream synthetic route of [ 402-43-7 ]

[ 402-43-7 ] Synthesis Path-Upstream   1~51

  • 1
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YieldReaction ConditionsOperation in experiment
96%
Stage #1: With sodium t-butanolate In tetrahydrofuran; toluene at 110℃; for 8 h;
Stage #2: With hydrogenchloride In water
Stage #3: With sodium hydroxide In water
Example 5 Bromobenzotrifluoride (22.5 g, 100 mmol) and piperazine (12.9 g, 150 mmol) were dissolved in 200 ml of toluene, and degassed at room temperature by passing nitrogen through for 15 min. Dry sodium tert-butoxide (13.5 g, 140 mmol) was added and the mixture was degassed for a further 10 min. In a separate vessel, [2-(2,4,6-triisopropylphenyl)phenyl]dicyclohexylphosphine (95 mg, 0.2 mmol) and palladium acetate (23 mg, 0.1 mmol) were stirred under nitrogen in 10 ml of degassed tetrahydrofuran. After 30 min, this catalyst solution was introduced dropwise at room temperature into the larger flask with the aid of a transfer needle. On completion of addition, the reaction was heated to internal temperature 110° C. After 8 h, the reaction was allowed to cool to 50° C. and the precipitated solid was filtered off. The filtrate was extracted with dilute hydrochloric acid at pH 3. The aqueous phase was removed and adjusted to pH 10 with the aid of sodium hydroxide solution. The precipitated white solid was filtered off and dried under reduced pressure. 22.1 g (96 mmol, 96percent of theory) of N-(4-trifluoromethylphenyl)piperazine were obtained. The product content of the solid was determined to be >99percent by quantitative proton NMR.
68% With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 70℃; for 2 h; Inert atmosphere [0705] The mixture of 1-bromo-4-(trifluoromethyl)benzene (15 g, 67 mmol), piperazine (28.8 g, 334.4 mmol, 5 eq.), Pd2(dba)3 (1.4 g, 1.53 mmol, 2 mol percent), BINAP (420 mg, 0.67 mmol, 1 mol percent) and t-BuONa (12.9 g, 134.2 mmol, 2 eq.) in toluene (200 ml) was stirred for 2 hours at 70° C. under nitrogen. Then the solids were filtered off and the mixture was concentrated under vacuum to give a residue, which was purified by silica gel column chromatography using 1percent 5percent methanol in dichloromethane to afford 1-[4-(trifluoromethyl)phenyl]piperazine as a dark red solid (10.5 g, 68percent). (ES, m/z): [M+H]+ 231.1; 1H NMR (300 MHz, CDCl3): δ 7.48 (d, J=8.7 Hz, 2H), 6.92 (d, J=8.7 Hz, 2H), 3.32-3.20 (m, 4H), 3.04-3.01 (m, 4H)
Reference: [1] Patent: US2005/250791, 2005, A1, . Location in patent: Page/Page column 4
[2] Patent: US2014/142114, 2014, A1, . Location in patent: Paragraph 0704; 0705
[3] Journal of the American Chemical Society, 2018, vol. 140, # 24, p. 7667 - 7673
[4] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 11, p. 1375 - 1377
  • 2
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  • [ 30459-17-7 ]
Reference: [1] Patent: WO2011/28947, 2011, A2,
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 24, p. 10158 - 10170
  • 3
  • [ 18293-53-3 ]
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  • [ 2338-75-2 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 45, p. 15824 - 15832
  • 4
  • [ 928664-98-6 ]
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  • [ 2338-75-2 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 18, p. 6948 - 6951
  • 5
  • [ 402-43-7 ]
  • [ 13406-29-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 18, p. 4069 - 4081
[2] Journal of Organic Chemistry, 1991, vol. 56, # 8, p. 2762 - 2769
[3] Chemische Berichte, 1984, vol. 117, # 9, p. 2791 - 2802
[4] Journal of Fluorine Chemistry, 1980, vol. 15, p. 239 - 244
[5] Chemical Communications, 2016, vol. 52, # 97, p. 14019 - 14022
[6] Organic Letters, 2017, vol. 19, # 19, p. 5434 - 5437
  • 6
  • [ 402-43-7 ]
  • [ 7719-12-2 ]
  • [ 13406-29-6 ]
YieldReaction ConditionsOperation in experiment
35% With hydrogenchloride; n-butyllithium In diethyl ether; hexane; water PREPARATION OF TRIS(4-TRIFLUOROMETHYLPHENYL)PHOSPHINE (R=4-trifluomethylphenyl)
8 grams of 4-bromobenzotrifluoride were dissolved in 45 milliliters of anhydrous diethylether at 0° C. under a nitrogen atmosphere.
14 milliliters of a 2.5 M solution of n-butyllithium in hexane were then added to the solution via syringe, with stirring, over a 10 minute period.
The solution was stirred for 30 minutes at 0° C., and then a solution of 1 milliliter of phosphorous trichloride in 15 milliliters of diethylether was added to the solution dropwise over a 50 minute period.
The resulting mixture was warmed to room temperature and stirred for 21/2 hours, then quenched with 50 milliliters of a 5 percent solution of hydrochloric acid.
The organic phase of the mixture was washed with 50 milliliters of water, followed by 50 milliliters of aqueous sodium chloride solution.
The organic phase was then dried over magnesium sulfate, filtered, and concentrated on a rotavap (rotary evaporator).
The resulting product was a red-orange oil, yield 5.31 grams.
The product included a triarylphosphine oxide side-product.
The side-product was removed by precipitation by the addition of hexane, followed by filtration of the side product.
The hexane solvent was removed on a rotavap, and the final product was an orange oil which crystallized upon standing.
The triarylphosphine product was purified by recrystallization from methanol.
The final yield of the triarylphosphine product was
1.95 grams (yield 35percent).
Reference: [1] Patent: US5194652, 1993, A,
  • 7
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  • [ 75-24-1 ]
  • [ 3972-65-4 ]
Reference: [1] Chemical Communications, 2009, # 40, p. 6011 - 6013
  • 8
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  • [ 104863-65-2 ]
  • [ 711-33-1 ]
Reference: [1] Angewandte Chemie, International Edition, 2009, vol. 48, p. 4543 - 4545[2] Angewandte Chemie, 2009, vol. 121, p. 4613 - 4615
  • 9
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Reference: [1] Journal of Organometallic Chemistry, 1997, vol. 533, # 1-2, p. 13 - 23
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  • [ 79-03-8 ]
  • [ 711-33-1 ]
Reference: [1] Canadian Journal of Chemistry, 1963, vol. 41, p. 1260 - 1264
  • 11
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  • [ 7657-08-1 ]
Reference: [1] Indian Journal of Chemistry, 1973, vol. 11, p. 1000 - 1002
  • 12
  • [ 201230-82-2 ]
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  • [ 77287-34-4 ]
  • [ 1801-10-1 ]
  • [ 1533-01-3 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4311 - 4315
  • 13
  • [ 1833-53-0 ]
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  • [ 713-45-1 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 7, p. 1213 - 1216
  • 14
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  • [ 123-54-6 ]
  • [ 713-45-1 ]
Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 24, p. 8273 - 8275
  • 15
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  • [ 75-56-9 ]
  • [ 713-45-1 ]
Reference: [1] Journal of the American Chemical Society, 1966, vol. 88, p. 5809 - 5816
  • 16
  • [ 201230-82-2 ]
  • [ 402-43-7 ]
  • [ 1891-90-3 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 16, p. 4454 - 4457
[2] Advanced Synthesis and Catalysis, 2012, vol. 354, # 16, p. 3065 - 3070
[3] Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4311 - 4315
[4] Chemistry - A European Journal, 2010, vol. 16, # 32, p. 9750 - 9753
[5] Chemistry - An Asian Journal, 2010, vol. 5, # 10, p. 2168 - 2172
[6] Tetrahedron Letters, 2013, vol. 54, # 24, p. 3040 - 3042
  • 17
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  • [ 1891-90-3 ]
YieldReaction ConditionsOperation in experiment
92% With 1H-imidazole; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; ammonium chloride; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 90℃; for 3 h; Sealed tube General procedure: To a stirred solution of aryl halide (Br/I) (1 mmol) in dry dioxane in a 25 mL sealed tube, was added Pd(OAc)2 (5 molpercent), dppf (6 mol percent), DIPEA (2 mmol), imidazole (0.25 mmol), ammonium chloride (2 mmol) and then Co2(CO)8 (0.3 mmol). The seal tube was closed immediately and stirred at 90 °C for 3h. After the reaction time the reaction mixture was cooled to room temperature. The reaction mixture was filtered through celite pad and washed with dioxane, the filtrate was concentrated under reduced pressure and the residue obtained was purified by column chromatography.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 34, p. 4864 - 4867
  • 18
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  • [ 1891-90-3 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 27, p. 21001 - 21004
  • 19
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  • [ 455-18-5 ]
  • [ 1891-90-3 ]
Reference: [1] Organometallics, 2015, vol. 34, # 10, p. 1942 - 1956
  • 20
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  • [ 455-18-5 ]
  • [ 1891-90-3 ]
Reference: [1] Organometallics, 2012, vol. 31, # 2, p. 729 - 738
  • 21
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Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 7, p. 1197 - 1200
  • 22
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  • [ 1483-56-3 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 16, p. 2767 - 2770
[2] Patent: US2007/213314, 2007, A1, . Location in patent: Page/Page column 33
[3] Patent: US2007/213371, 2007, A1, . Location in patent: Page/Page column 36
  • 23
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  • [ 2968-93-6 ]
Reference: [1] Journal of medicinal chemistry, 1963, vol. 6, p. 506 - 508
  • 24
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  • [ 6148-64-7 ]
  • [ 721-63-1 ]
YieldReaction ConditionsOperation in experiment
87% With dmap; bis(η3-allyl-μ-chloropalladium(II)); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,3,5-trimethyl-benzene at 140℃; for 20 h; Inert atmosphere General procedure: after standard cycles of evacuation and back-filling with dry and pure nitrogen, an oven-dried Schlenk tube equipped with a magnetic stirring bar was charged with Pd source (see Table 1, Table 2, Table 3 and Table 4), ligand (see Table 1, Table 2, Table 3 and Table 4), N,N-dimethylpyridin-4-amine (DMAP, see Table 1, Table 2, Table 3 and Table 4), and ethyl potassium malonate (see Table 1, Table 2, Table 3 and Table 4). The tube was evacuated and backfilled with argon (this procedure was repeated three times). Under a counter flow of argon, aryl halide (see Table 1, Table 2, Table 3 and Table 4) and solvent (see Table 1, Table 2, Table 3 and Table 4) were added by syringe. The tube was sealed and stirred at room temperature for 10 min. Then the tube was connected to the Schlenk line, which was full of argon, stirred in a preheated oil bath (140-150 °C) for the appointed time (20-25 h). Upon completion of the reaction, the mixture was cooled to room temperature and diluted with diethyl ether, and the yields were determined by gas chromatography using 1,3-dimethoxybenzene as the internal standard.
Reference: [1] Tetrahedron, 2012, vol. 68, # 9, p. 2113 - 2120
  • 25
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Reference: [1] Advanced Synthesis and Catalysis, 2011, vol. 353, # 9, p. 1565 - 1574
  • 26
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Reference: [1] Journal of Fluorine Chemistry, 1988, vol. 40, p. 81 - 98
  • 27
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  • [ 57478-19-0 ]
YieldReaction ConditionsOperation in experiment
27% With potassium carbonate In dimethyl sulfoxide 4-(4-Trifluormethylphenoxy)aniline:
To a stirred solution of 4-trifluormethylbromobenzene (11.2 g, 50 mmol) in dimethylsulphoxide (50 mL) is added powdered potassium carbonate (3.4g, 60 mmol) and 4-aAminophenol (6.6 g, 55 mmol).
The suspension is heated at 90°C for 4.5 h, then poured into water, extracted with di-isopropylether, filtered, decanted, the organic phase washed with water, dried (magnesium sulphate) and evaporated to give 9.6 g of a brown oil.
To this triturated with pentane, the resulting precipitate filtered, washed with pentane and dried to give 3.3 g of the title compound (27percent, mp. 72 °C).
Reference: [1] Patent: EP1275301, 2003, A1,
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  • [ 15929-43-8 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 42, p. 5550 - 5554
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Reference: [1] Synthetic Communications, 2003, vol. 33, # 2, p. 324 - 330
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YieldReaction ConditionsOperation in experiment
54%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at -78 - 20℃; for 12 h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 1 h;
[Embodiment 4]; In this embodiment, a synthesis method of9-[4-(carbazol-9-yl)phenyl]-10-(4-trifluoromethylphenyl)anthracene (CF3CzPA) represented by a structural formula (42) will be described.; [Step 1] Synthesis of 9-bromo-10-(4-trifluoromethylphenyl)anthracene; (i) Synthesis of 4-trifluoromethylphenylboronic acid; A synthesis scheme of 4-trifluoromethylphenylboronic acid is shown in (E-I). [0282]1 ) n-BuLi, THF, -780C[0283] 33 g (0.15 mol) of 4-bromotrifluoromethylbenzen was put into a 500-mL three-neck flask, and nitrogen substitution in the system was carried out. Then, 200 mL of tetrahydrofuran (THF) was added thereto, and the mixture was stirred. This mixture solution was stirred at -78 0C, and 100 mL (0.16 mol) of n-butyllithium (1.6 mol/L) was dropped into the solution through a dropping funnel. After that, the obtained solution was stirred at the same temperature for 1 hour, and 22.3 mL (0.20 mol) of trimethyl borate was added to be stirred for about 12 hours while the reaction <n="96"/>temperature was allowed to gradually increase to the room temperature. Then, 100 mL of dilute hydrochloric acid (1 rnol/L) was added to the reaction solution, and the solution was stirred for 1 hour. A water layer of the mixture was extracted using ethyl acetate three times, the extracted solution and an organic layer were washed together one time using saturated saline, and the organic layer was dried with magnesium sulfate. The mixture was filtrated naturally to remove magnesium sulfate, and the filtrate was condensed to obtain a solid. The solid was washed with chloroform, whereby 15 g of a white solid, which was a target matter, was obtained with the yield of 54 percent.
Reference: [1] Patent: WO2008/26614, 2008, A1, . Location in patent: Page/Page column 93-95
[2] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 17, p. 2513 - 2523
[3] Organic and Biomolecular Chemistry, 2012, vol. 10, # 33, p. 6693 - 6704
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 9, p. 1919 - 1922
[5] Journal of Organometallic Chemistry, 2017, vol. 846, p. 305 - 311
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Reference: [1] Organic Letters, 2011, vol. 13, # 17, p. 4479 - 4481
[2] Organic and Biomolecular Chemistry, 2012, vol. 10, # 33, p. 6693 - 6704
[3] Organic Letters, 2005, vol. 7, # 21, p. 4757 - 4759
[4] Tetrahedron, 2004, vol. 60, # 25, p. 5373 - 5382
[5] Patent: US5739166, 1998, A,
[6] Chemistry - A European Journal, 2011, vol. 17, # 48, p. 13502 - 13509
[7] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673
[8] Journal of the American Chemical Society, 2013, vol. 135, # 4, p. 1264 - 1267
[9] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439
[10] Chemistry - A European Journal, 2013, vol. 19, # 46, p. 15565 - 15571
[11] Patent: WO2003/101381, 2003, A2, . Location in patent: Page 72-73
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Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 10999 - 11003[2] Angew. Chem., 2018, # 130, p. 11165 - 11169,5
[3] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
[4] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
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YieldReaction ConditionsOperation in experiment
35% With magnesium In tetrahydrofuran; hexane; ethyl acetate EXAMPLE 52
Synthesis of 4-(trifluoromethyl)phenylboronic acid
An oven dried Schlenk tube was charged with magnesium turnings (766 mg, 31.5 mmol), evacuated, and backfilled with argon.
To the reaction vessel was added 10 mL of ether followed by 4-(trifluoromethyl)phenyl bromide (4.20 mL, 30.0 mmol).
The reaction mixture was stirred without external heating for 1 hour, during which time an exotherm occurred and then subsided.
The solution was diluted with ether (10 mL) and transferred via cannula to a flask containing triisopropylborate (13.8 mL, 60.0 mmol) in 1:1 THF/ether (20 mL) at -78° C.
The resulting reaction mixture was kept at -78° C. for 15 minutes and then was allowed to warm to room temperature.
After stirring at room temperature for 15 minutes, the reaction mixture was poured onto 2.0 M HCl (60 mL).
The mixture was transferred to a separatory funnel, extracted with ethyl acetate (60 mL), washed with water (60 mL), and brine (60 mL).
The organic solution was dried over anhydrous sodium sulfate and concentrated in vacuo.
The crude material was dissolved in 2:1 hexane/ethyl acetate (90 ml,) and activated charcoal was added.
The mixture was filtered and the product crystallized upon cooling.
The crystals were collected by filtration to afford 1.98 g (35percent) of pale yellow needles.
35% With magnesium In tetrahydrofuran; hexane; ethyl acetate Example 52
Synthesis of 4-(trifluoromethyl)phenylboronic acid
An oven dried Schlenk tube was charged with magnesium turnings (766 mg, 31.5 mmol), evacuated, and backfilled with argon.
To the reaction vessel was added 10 mL of ether followed by 4-(trifluoromethyl)phenyl bromide (4.20 mL, 30.0 mmol).
The reaction mixture was stirred without external heating for 1 hour, during which time an exotherm occurred and then subsided.
The solution was diluted with ether (10 mL) and transferred via cannula to a flask containing triisopropylborate (13.8 mL, 60.0 mmol) in 1:1 THF/ether (20 mL) at -78° C.
The resulting reaction mixture was kept at -78° C. for 15 minutes and then was allowed to warm to room temperature.
After stirring at room temperature for 15 minutes, the reaction mixture was poured onto 2.0 M HCl (60 mL).
The mixture was transferred to a separatory funnel, extracted with ethyl acetate (60 mL), washed with water (60 mL), and brine (60 mL).
The organic solution was dried over anhydrous sodium sulfate and concentrated in vacuo.
The crude material was dissolved in 2:1 hexane/ethyl acetate (90 mL) and activated charcoal was added.
The mixture was filtered and the product crystallized upon cooling.
The crystals were collected by filtration to afford 1.98 g (35percent) of pale yellow needles.
Reference: [1] Patent: US6307087, 2001, B1,
[2] Patent: US2004/171833, 2004, A1,
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Reference: [1] Patent: US6303593, 2001, B1,
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Reference: [1] Patent: US2003/109700, 2003, A1,
[2] Patent: US6197798, 2001, B1,
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, p. 715 - 720
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Reference: [1] Synthesis (Germany), 2017, vol. 49, # 4, p. 736 - 744
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YieldReaction ConditionsOperation in experiment
84% With 1H-imidazole; palladium diacetate; triethylamine; [5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphane; magnesium chloride In tetrahydrofuran at 90℃; for 0.5 h; Microwave irradiation To a stirred mixture of aryl or heteroaryl halide(Br, I) (0.5 mmol), potassium mono ethyl malonate (0.75 mmol) in THF (10 mL) taken in a 30 mL microwave vial, was added Pd(OAc)2(5 molpercent), Xantphos (5 mol percent), MgCl2 (0.75), Et3N ( 0.75mmol), imidazole (1 mmol) followed by Co2(CO)8 (0.15mmol). The vial was sealed immediately and microwave irradiated at 90°C for 30min. The reaction mixture was concentrated and diluted with ethyl acetate and water. The ethyl acetate layer was separated, dried over sodium sulphate and concentrated. The crude product obtained was purified by column chromatography to get the pure compound.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 25, p. 3525 - 3528
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  • [ 68-12-2 ]
  • [ 102684-91-3 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 16, p. 5346 - 5354
  • 40
  • [ 3984-22-3 ]
  • [ 402-43-7 ]
  • [ 53473-36-2 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 50, p. 11533 - 11540
  • 41
  • [ 402-43-7 ]
  • [ 149105-19-1 ]
  • [ 84392-17-6 ]
Reference: [1] Synthesis, 2002, # 8, p. 1043 - 1046
  • 42
  • [ 402-43-7 ]
  • [ 14047-29-1 ]
  • [ 195457-71-7 ]
Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5163 - 5173
[2] Patent: EP1657242, 2006, A1, . Location in patent: Page/Page column 28-29
[3] Patent: US2007/82952, 2007, A1, . Location in patent: Page/Page column 6
  • 43
  • [ 402-43-7 ]
  • [ 195457-71-7 ]
Reference: [1] Journal of Organometallic Chemistry, 2001, vol. 624, # 1-2, p. 208 - 216
  • 44
  • [ 402-43-7 ]
  • [ 87199-17-5 ]
  • [ 90035-34-0 ]
YieldReaction ConditionsOperation in experiment
12.1 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 85℃; for 2 h; Reference Example 6-2
4'-(Trifluoromethyl)biphenyl-4-carbaldehyde
A mixture of 4-bromobenazotrifluoride (10.0 g), 4-formylphenylboronic acid (7.33 g), tetrakis(triphenylphosphine)palladium(0) (308 mg), potassium carbonate (30.7 g), tetrahydrofuran (300 mL) and water (100 mL) was stirred at 85°C for 2 hours.
After cooling the reaction mixture to room temperature, water was added to it, which was then extracted with ethyl acetate twice and the combined organic layers were washed with saturated brine.
After adding anhydrous magnesium sulfate to the organic layers, the desiccant was removed by filtration and the filtrate was concentrated under reduced pressure.
The resulting residue was dissolved in n-hexane (60 mL) with heating and thereafter cooled to 0°C.
The resulting precipitate was recovered by filtration to give the titled compound as a gray solid (12.1 g).
1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.71 - 7.80 (m, 6 H) 7.96 - 8.03 (m, 2 H) 10.09 (s, 1 H).
MS EI posi: 250[M]+.
Reference: [1] Patent: WO2005/3118, 2005, A1, . Location in patent: Page/Page column 34
[2] Patent: WO2006/63791, 2006, A1, . Location in patent: Page/Page column 27
[3] Patent: WO2006/63811, 2006, A2, . Location in patent: Page/Page column 30
[4] Patent: WO2006/63812, 2006, A1, . Location in patent: Page/Page column 24
[5] Journal of the American Chemical Society, 2009, vol. 131, p. 8163 - 8172
[6] Chemical Communications, 2015, vol. 51, # 40, p. 8439 - 8441
[7] Patent: EP2881384, 2015, A1, . Location in patent: Paragraph 0295; 0296
  • 45
  • [ 402-43-7 ]
  • [ 128376-64-7 ]
  • [ 90035-34-0 ]
YieldReaction ConditionsOperation in experiment
90.1% With potassium carbonate In tolueneInert atmosphere; Reflux 4'-trifiuoromethy.biphenyi-4-carbaldehyde (Compound 25}Pd(PPh3)4 (6 g) was added to a mixture of 4-fbrmyiphenylboronic acid plnacoS cyclic ester (53 g, 0,22 mol), 4-trifluoromethylbromobenzene(50 g, 0.22 mol), and potassium carbonate (63 g, 0.46 mol) In toluene (2 L) under nitrogen protection. The mixture was refiuxed overnight. After cooling to room temperature, the solvent was removed under vacuum. To the residue were added water (l L) and ethyl acetate (1 L), The organic phase was collected, and the water phase was extracted with ethyl acetate (1 L x2). The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by HPFC (PE: EA = 50: 1) to afford the title compound (50.2 g, 90.1percent). LC- S: 251.2 (M+l).
Reference: [1] Patent: WO2012/130299, 2012, A1, . Location in patent: Page/Page column 113
  • 46
  • [ 402-43-7 ]
  • [ 619-66-9 ]
  • [ 90035-34-0 ]
Reference: [1] Patent: EP1216225, 2005, B1, . Location in patent: Page/Page column 43
  • 47
  • [ 402-43-7 ]
  • [ 317318-97-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 1, p. 49 - 54
  • 48
  • [ 5382-16-1 ]
  • [ 402-43-7 ]
  • [ 681508-70-3 ]
YieldReaction ConditionsOperation in experiment
59% With sodium t-butanolate In toluene at 120℃; for 1 h; Microwave irradiation Reference Example 4 Synthesis of Compound 10 [Show Image] [Show Image] Under the nitrogen atmosphere, toluene was added to BINAP (187 mg, 0.3 mmol), Pd2(dba)3 (92 mg, 0.1 mmol), sodium tert-butoxide (1.19 g, 12.0 mmol), Compound 8 (1.14 g, 11.2 mmol), and Compound 9 (1.36 ml, 10.0 mmol) to react them at 120°C for 1 hour under microwave irradiation. The reaction solution was filtered using Celite, and the solid was washed with ethyl acetate. The filtrate and the washing solution were combined, and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain Compound 10 (1.45 g, yield 59percent). mp 97-98°C 1H-NMR (CDCl3 / TMS) δppm: 1.49-1.56 (m, 2H), 1.62-1.74 (m, 2H), 2.03 (brs, 2H), 3.03-3.10 (m, 2H), 3.63-3.71 (m, 2H), 3.93 (brs, 1H), 6.97 (br, 2H), 7.48 (d, J = 8.7Hz, 2H).
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 24, p. 7667 - 7673
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 13088 - 13093[3] Angew. Chem., 2017, vol. 129, p. 13268 - 13273,6
[4] Patent: EP1988077, 2008, A1, . Location in patent: Page/Page column 63-64
[5] Patent: WO2010/115688, 2010, A1, . Location in patent: Page/Page column 127
  • 49
  • [ 402-43-7 ]
  • [ 59016-93-2 ]
  • [ 457889-46-2 ]
Reference: [1] Patent: US2004/209936, 2004, A1,
[2] Patent: US2003/225158, 2003, A1, . Location in patent: Page 24
  • 50
  • [ 402-43-7 ]
  • [ 640280-28-0 ]
YieldReaction ConditionsOperation in experiment
85% at 20℃; for 15 h; 4-Bromobenzotrifluoride (35 ml, 0.25 mol) was dissolved in 100 ml of triflic acid at room temperature. N-iodosuccinimide (59 g, 0.26 mol) was added portionwise over 5 minutes and the dark mixture was stirred for an additional 15 hours at room temperature. The reaction mixture was put onto ice (300 g) and after the ice had melted, the aqueous phase was extracted with 3 portions (100 ml) of diethyl ether. The organic phases were combined, washed with saturated sodium carbonate, water and brine and dried over magnesium sulfate. After filtration and evaporation of the solvent, the remaining liquid was distilled under vacuum (0.25 mbar) to yield 4-bromo-3-iodobenzotrifluoride (85 g, 85 percent) as a clear liquid, boiling point: 62-64 0C.
Reference: [1] Heterocycles, 2007, vol. 74, # C, p. 683 - 700
[2] Angewandte Chemie - International Edition, 2008, vol. 47, # 42, p. 8108 - 8111
[3] Chemistry - A European Journal, 2016, vol. 22, # 28, p. 9687 - 9692
[4] Patent: WO2006/8558, 2006, A1, . Location in patent: Page/Page column 45
[5] Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480
[6] Journal of the American Chemical Society, 2014, vol. 136, # 25, p. 8887 - 8890
[7] Journal of the American Chemical Society, 2015, vol. 137, # 36, p. 11574 - 11577
  • 51
  • [ 402-43-7 ]
  • [ 75927-49-0 ]
  • [ 1242770-50-8 ]
Reference: [1] New Journal of Chemistry, 2017, vol. 41, # 8, p. 3172 - 3176
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