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[ CAS No. 651-83-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Chemical Structure| 651-83-2

Chemical Structure| 651-83-2

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Quality Control of [ 651-83-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 651-83-2 ]

SDS Specification

Alternatived Products of [ 651-83-2 ]

Product Details of [ 651-83-2 ]

CAS No. :	651-83-2	MDL No. :	MFCD00091518
Formula :	C₇H₂F₇N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FJOACTZFMHZHSC-UHFFFAOYSA-N
M.W :	233.09	Pubchem ID :	616257
Synonyms :

Safety of [ 651-83-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H227-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 651-83-2 ]

* 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 [ 651-83-2 ]
Downstream synthetic route of [ 651-83-2 ]

[ 651-83-2 ] Synthesis Path-Upstream 1~3

1
[ 651-83-2 ]
[ 700-17-4 ]

Yield	Reaction Conditions	Operation in experiment
66%	at 150℃; for 2 h;	Aniline 7 (15 g, 64 mmol) in concentrated H₂SO₄ (50 mL) was stirred with a condenser at 150 °C for 2 h. Then, H₂O (100 mL) was added into the reaction flask, and the reaction product was separated by steam distillation. The distillate was extracted with CH₂Cl₂ (3×50 mL), washed with H₂O (50 mL) and dried (MgSO₄). After evaporation of the solvent in vacuo, the title product (7 g, 66 percent) was obtained as light yellow liquid (the ¹H and ¹⁹F NMR spectra closely match the literature data [36]. ν_max (KBr): 3501, 3414 (NH₂), 1664, 1618, 1524, 1400, 1269, 1178, 1090, 887, 804, 716 cm⁻¹; ¹H NMR (300.13 MHz, CDCl₃): δ=6.36 (tt, 1H, J_H,_F3=10.5; J_H,_F2=7.3Hz, H_ar), 4.03 (br s, 2H, NH₂); ¹³C NMR (100.62 MHz, CDCl₃): δ=146.2 (dm, ¹J_C3,_F=243.4, ²J_C3,_F=12.6Hz, C³), 136.3 (ddt, ¹J_C2,_F=238.1, ²J_C2,_F=16.2Hz, C²), 126.7 (tt, ²J_C1,_F=14.3, ³J_C1,_F=4.3Hz, C¹), 93.0 (t, ²J_C4,_F=23.2Hz, C⁴); ¹⁹F NMR (282.37 MHz, CDCl₃): δ=−142.9 (m, 2F, J_F3,_F2=24, J_F3,_H=10Hz, F³), −163.3 (m, 2F, J_F2,_F3=24, J_F2,_H=7Hz, F²); HRMS (EI): ⁺, found 165.0205. C₆H₃F₄N requires 165.0196.

Reference： [1] Journal of Fluorine Chemistry, 2016, vol. 188, p. 85 - 98

2
[ 651-83-2 ]
[ 700-17-4 ]

Reference： [1] Journal of Fluorine Chemistry, 2016, vol. 188, p. 85 - 98

3
[ 651-83-2 ]
[ 363-80-4 ]

Reference： [1] Tetrahedron, 2017, vol. 73, # 9, p. 1219 - 1229

[ 651-83-2 ] Synthesis Path-Downstream 1~65

1
[ 434-64-0 ]
[ 651-83-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With ammonia; at 20℃; for 6h;Autoclave;	1,2,3,4,5-Pentafluoro-6-(trifluoromethyl)benzene (50 g, 0.3 mol) and liquid ammonia were placed into the autoclave (volumetric capability 0.1 L). The reaction mixture was stirred at room temperature (r.t.) for 6 h. After completion of ammonia evaporation, H2O (50 mL) was added to the residue. The reaction product was separated by steam distillation. The distillate was extracted with CH2Cl2 (2100 mL) and dried (MgSO4). After evaporation of the solvent in vacuo, the title product (47 g, 93 %) was obtained as colorless liquid (the 1H and 19F NMR spectra agree well with the literature data [35].
72%	With ammonium hydroxide; In 1,4-dioxane; water; at 80℃;Sealed tube;	Preparation of 2,3,5,6-Tetrafluoro-4-(triluoromethyl)aniline [1] To a solution of octafluorotoluene (30 mL) in 1,4-dioxane (79 mL) was added aq. NH4OH (53 mL, 28% w/w), and the reaction flask was sealed and heated to 80 C. The reaction mixture was stirred until the substrate was completely consumed, as verified by GCMS and TLC. The mixture was then cooled, and 1,4-dioxane was removed in vacuo. The resultant mixture was extracted with ethyl acetate (3*100 mL), and then concentrated in vacuo. The crude mixture was purified by column chromatography (hexanes?hexanes:ethyl acetate=4:1) to afford 2,3,5,6-tetrafluoro-4-(trifluoromethyl)aniline as a colorless liquid (72 g, 72%).

Reference： [1]Journal of Fluorine Chemistry,2016,vol. 188,p. 85 - 98
[2]Chemistry Letters,2011,vol. 40,p. 1004 - 1006
[3]Angewandte Chemie - International Edition,2011,vol. 50,p. 9081 - 9084
[4]Patent: US2014/18566,2014,A1 .Location in patent: Paragraph 0135; 0136
[5]Journal of the American Chemical Society,2017,vol. 139,p. 13092 - 13101
[6]Australian Journal of Chemistry,2013,vol. 66,p. 145 - 150
[7]Journal of Fluorine Chemistry,1982,vol. 20,p. 507 - 514
[8]Journal of the Chemical Society,1962,p. 1801 - 1805
[9]Journal of Organic Chemistry USSR (English Translation),1988,vol. 24,p. 2267 - 2272
Zhurnal Organicheskoi Khimii,1988,vol. 24,p. 2513 - 2518
[10]Journal of the Chemical Society,1962,p. 1801 - 1805
[11]Journal of Fluorine Chemistry,2008,vol. 129,p. 998 - 1002

2
[ 651-83-2 ]
[ 63995-40-4 ]

Reference： [1]Journal of general chemistry of the USSR,1985,vol. 55,p. 849 - 864
Zhurnal Obshchei Khimii,1985,vol. 55,p. 953 - 970

3
[ 651-83-2 ]
[ 63995-48-2 ]

Reference： [1]Journal of general chemistry of the USSR,1985,vol. 55,p. 849 - 864
Zhurnal Obshchei Khimii,1985,vol. 55,p. 953 - 970
[2]Journal of Organic Chemistry USSR (English Translation),1980,vol. 16,p. 717 - 722
Zhurnal Organicheskoi Khimii,1980,vol. 16,p. 817 - 822

4
[ 651-83-2 ]
[ 98583-25-6 ]

Reference： [1]Journal of Fluorine Chemistry,1988,vol. 39,p. 373 - 384
[2]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1986,vol. 35,p. 1391 - 1397
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1986,p. 1537 - 1544

5
[ 651-83-2 ]
[ 98-88-4 ]
[ 80588-64-3 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 20℃; for 28h;Reflux;	General procedure: General Procedure for the Preparation of Benzamides: [0138] An acid chloride (20 mmol), prepared from the corresponding carboxylic acid and oxalyl chloride or thionyl chloride, was added to a vigorously stirred solution of <strong>[651-83-2]2,3,5,6-tetrafluoro-4-(trifluoromethyl)aniline</strong> (21 mmol) in toluene (3 mL). The reaction mixture was stirred for 24 h under reflux, and then stirred at room temperature for 4 h. The product mixture was concentrated in vacuo and was recrystallized from ethyl acetate/hexane (100 C. to -30 C.) to give the amide. The prepared substrates were used without further purification provided that they appeared pure by TLC, GCMS and NMR. The directing group peaks in the 13C NMR spectra were not reported due to the complex splitting of the corresponding peaks from C-F coupling. However, the presence of F atoms was verified by the 19F NMR spectra. N-(2,3,5,6-Tetrafluoro-4-(trifluoromethyl)phenyl)benzamide (1) [0139] 1H NMR (400 MHz, (CD3)2SO) delta 10.92 (s, 1H), 8.02 (d, J=8.3 Hz, 2H), 7.67 (t, J=7.4 Hz, 1H), 7.58 (t, J=7.6 Hz, 2H); 13C NMR (100 MHz, (CD3)2SO)S 165.15, 132.80, 132.13, 128.71, 128.22; 19F NMR (375 MHz, (CD3)2SO) delta -54.75 (t, J=20.7 Hz, 3F), -142.06 to -142.34 (m, 4F); HRMS (ESI-TOF) Calcd for C14H7F7NO (MH+): 338.0410. found: 338.0423.

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1981,vol. 17,p. 1807 - 1813
Zhurnal Organicheskoi Khimii,1981,vol. 17,p. 2025 - 2031
[2]Journal of the American Chemical Society,2011,vol. 133,p. 7652 - 7655
[3]Angewandte Chemie - International Edition,2011,vol. 50,p. 9081 - 9084
[4]Chemistry Letters,2011,vol. 40,p. 1004 - 1006
[5]Journal of the American Chemical Society,2012,vol. 134,p. 11948 - 11951
[6]Patent: US2014/18566,2014,A1 .Location in patent: Paragraph 0137; 0138; 0139;
[7]Tetrahedron Letters,2020

6
[ 100758-21-2 ]
[ 651-83-2 ]
[ 65-85-0 ]

Reference： [1]Journal of Fluorine Chemistry,1985,vol. 28,p. 23

7
pentafluorobenzylidene 4-trifluoromethyl-2,3,5,6-tetrafluoroaniline [ No CAS ]
[ 602-94-8 ]
[ 651-83-2 ]

Reference： [1]Journal of Fluorine Chemistry,1985,vol. 28,p. 23

8
[ 651-83-2 ]
[ 108-67-8 ]
[ 93832-48-5 ]

Reference： [1]Journal of Fluorine Chemistry,1988,vol. 40,p. 147 - 170
[2]Journal of the Chemical Society. Chemical communications,1984,p. 832 - 833

9
[ 434-64-0 ]
[ 38727-32-1 ]
[ 651-83-2 ]

Reference： [1]Journal of Fluorine Chemistry,1995,vol. 75,p. 169 - 172
[2]Journal of Fluorine Chemistry,1995,vol. 75,p. 169 - 172

10
[ 651-83-2 ]
[ 108-24-7 ]
N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)acetamide [ No CAS ]

Reference： [1]Tetrahedron,2017,vol. 73,p. 1219 - 1229
[2]Journal of the American Chemical Society,2017,vol. 139,p. 13092 - 13101
[3]Journal of Fluorine Chemistry,2001,vol. 110,p. 43 - 46
[4]Journal of the American Chemical Society,2014,vol. 136,p. 3002 - 3005

11
[ 651-83-2 ]
[ 186258-15-1 ]
[ 496951-29-2 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 319 - 326

12
[ 37942-07-7 ]
[ 651-83-2 ]
N-(3,5-di-tert-butylsalicylidene)-2,3,5,6-tetrafluoro-4-amino-α,α,α-trifluorotoluene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 10798 - 10799
[2]Russian Chemical Bulletin,2003,vol. 52,p. 1693 - 1697

13
[ 627-51-0 ]
[ 434-64-0 ]
2,3,5,6-tetrafluoro-4-trifluoromethy-1-vinylsulfanylbenzene [ No CAS ]
1-(3-butenylsulfanyl)-2,3,5,6-tetrafluoro-4-trifluoromethylbenzene [ No CAS ]
[ 38727-32-1 ]
[ 651-83-2 ]

Reference： [1]Russian Journal of Organic Chemistry,2005,vol. 41,p. 402 - 405

14
[ 627-51-0 ]
[ 651-83-2 ]
1-amino-2,5-di(vinylthio)-4-trifluoromethyl-3,6-difluorobenzene [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2005,vol. 41,p. 402 - 405
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2005,vol. 180,p. 1435 - 1436

15
[ 32315-10-9 ]
[ 651-83-2 ]
[ 1003887-74-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.5h;	A solution of 2,3,5,6-tetrafluoro-4-(trifluoromethyl)-benzenamine (140 mg, 0.6 mmol), DIEA (1.2 eq, 126 muL) in dichloromethane (0.5 mL) was added to a solution of triphosgene (0.37 eq, 66 mg) in DCM (0.5 mL) over 30 min via syringe pump. It was used without work-up.

Reference： [1]Patent: WO2008/11392,2008,A2 .Location in patent: Page/Page column 41

16
[ 651-83-2 ]
2,3,5-trifluoro-4-(trifluoromethyl)aniline [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2001,vol. 110,p. 43 - 46
[2]Journal of the American Chemical Society,2017,vol. 139,p. 13092 - 13101

17
[ 762-99-2 ]
[ 651-83-2 ]
bis[(3,5-di-tert-butylsalicylidene)-4-trifluoromethyl-2,3,5,6-tetrafluoroanilinato]titanium(IV) dichloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	In dichloromethane; at 20℃; for 20h;	50ml three-neck flask equipped with mechanical stirrer, argon inlet tube and dosing funnel was purged with dry argon and charged with solution containing 0,0448 G (0.10 mmol) of 3,5-di-tert- butylsalicylidene-4-trifluoromethyl-2,3, 5,6-tetrafluoroanilinate dissolved in 10 ml of methylene chloride. The solution containing 0,0118 g (0.05 mmol) of TiCl2(OiPr)2 in 50 ml of methylene chloride was added dropwise with stirring. The mixture was agitated for 20 hours at ambient temperature; solid product was filtered out from reaction mixture, washed with methylene chloride and toluene and dried in vacuum at 60C to remove residues of solvent with following purging with dry argon to give 0,0414 g of crystalline product. Yield 0, 0408 mmol (82%), IR, nu/cm-1 : (C=N) 1610; (Ti-0) 560; (Ti-N) 470 ; 1H NMR : &dela; 1,54 (s, 36H, tert-Bu), 6.90-7.53 (m, 4H, aromatic H), 9,89 (s, 2H, CH=N). Analysis found (%): C, 52.90 ; H, 4. 20; N, 4.41. Calculated for TiC44H42N2O2F14Cl2 (%) : C, 52.02 ; H, 4.14 ; N, 4.72.

Reference： [1]Patent: WO2004/92190,2004,A1 .Location in patent: Page/Page column 13

18
[ 651-83-2 ]
[ 90-02-8 ]
[ 657429-19-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With toluene-4-sulfonic acid; In toluene; for 20h;Heating / reflux;	50 ml the two neck flask was filled with 20 ml of toluene, 0,1990 g (0.85 mmol) of 3, 5-di-tert- butylsalicylic aldehyde, 0,0017 g (0.01 mmol) of p-toluenesulfonic acid and 0,1981 g (0.85 mmol) of <strong>[651-83-2]4-trifluoromethyl-2,3,5,6-tetrafluoroaniline</strong>. The mixture was heated with reflux for 20 hours, then solution was cooled to ambient temperature, filtered and the solvent was removed in vacuum resulting deep yellow oil. The product was dissolved in 20 ml of mixture hexane-ethyl acetate (5: 1) and purified by column chromatography using silica gel as absorbent and the mixture of hexane- ethyl acetate (5: 1) as the eluet resulting 0,2787 g of yellow oil. Yield 0, 6375 mmol (75 %), 1H NMR : delta 1.31-1.45 (s, 18H, tert-Bu), 7.52-7.72 (m, 2H, aromatic H), 9,84 (s, 1H, CH=N), 11.61 (s, IH, OH). Analysis found (%): C, 58. 64 ; H, 4.58 ; N, 3.15. Calculated for C22H22NOF7 (%) : C, 58. 80 ; H, 4. 68 ; N, 3.12.

Reference： [1]Patent: WO2004/92190,2004,A1 .Location in patent: Page/Page column 11-12

19
[ 1711-09-7 ]
[ 651-83-2 ]
[ 1300857-09-3 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 7652 - 7655
[2]Angewandte Chemie - International Edition,2011,vol. 50,p. 9081 - 9084
[3]Chemistry Letters,2011,vol. 40,p. 1004 - 1006
[4]Journal of the American Chemical Society,2012,vol. 134,p. 11948 - 11951
[5]Angewandte Chemie - International Edition,2015,vol. 54,p. 2497 - 2500
Angew. Chem.,2015,vol. 127,p. 2527 - 2530,4
[6]Journal of the American Chemical Society,2014,vol. 136,p. 13194 - 13197

20
[ 651-83-2 ]
[ 618-46-2 ]
[ 1300857-08-2 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 7652 - 7655
[2]Angewandte Chemie - International Edition,2011,vol. 50,p. 9081 - 9084
[3]Chemistry Letters,2011,vol. 40,p. 1004 - 1006
[4]Journal of the American Chemical Society,2012,vol. 134,p. 11948 - 11951
[5]Angewandte Chemie - International Edition,2015,vol. 54,p. 2497 - 2500
Angew. Chem.,2015,vol. 127,p. 2527 - 2530,4
[6]Tetrahedron Letters,2020

21
[ 651-83-2 ]
[ 933-88-0 ]
[ 1300857-03-7 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 7652 - 7655
[2]Angewandte Chemie - International Edition,2011,vol. 50,p. 9081 - 9084
[3]Chemistry Letters,2011,vol. 40,p. 1004 - 1006
[4]Journal of the American Chemical Society,2012,vol. 134,p. 11948 - 11951
[5]Journal of the American Chemical Society,2014,vol. 136,p. 13194 - 13197
[6]Tetrahedron Letters,2020

22
[ 651-83-2 ]
[ 80850-06-2 ]

Reference： [1]ChemSusChem,2012,vol. 5,p. 312 - 319

23
[ 651-83-2 ]
[ 1423543-36-5 ]

Reference： [1]Australian Journal of Chemistry,2013,vol. 66,p. 145 - 150

24
[ 6051-13-4 ]
[ 651-83-2 ]
[ 1425052-49-8 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 3387 - 3390

25
[ 6051-13-4 ]
[ 651-83-2 ]
[ 1425052-38-5 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 3387 - 3390

26
[ 651-83-2 ]
[ 99783-23-0 ]
[ 1425052-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride In toluene at 0 - 20℃; for 12.5h; Reflux; Inert atmosphere;

Reference： [1]He, Jian; Wasa, Masayuki; Chan, Kelvin S. L.; Yu, Jin-Quan [Journal of the American Chemical Society, 2013, vol. 135, # 9, p. 3387 - 3390]

27
[ 651-83-2 ]
[ 30091-13-5 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 5309 - 5313
Angew. Chem.,2013,vol. 125,p. 5417 - 5421,5

28
[ 651-83-2 ]
[ 645-45-4 ]
[ 1443771-38-7 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3440 - 3443

29
[ 651-83-2 ]
[ 41716-12-5 ]
[ 1446442-90-5 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 10326 - 10329

30
[ 651-83-2 ]
[ 41716-12-5 ]
[ 1446442-60-9 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 10326 - 10329

31
[ 651-83-2 ]
[ 84547-59-1 ]
[ 1446442-92-7 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 10326 - 10329

32
[ 651-83-2 ]
[ 84547-59-1 ]
[ 1005610-37-6 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 10326 - 10329

33
[ 651-83-2 ]
[ 1570134-48-3 ]
[ 1570135-41-9 ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 3354 - 3357

34
[ 651-83-2 ]
[ 4306-25-6 ]
[ 1582806-46-9 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; for 12h;Reflux;	To a 100 mL round-bottom flask were added the appropriate amino acid (20 mmol) , finely ground phthalic anhydride (20 mmol or 40 mmol in the synthesis of lysine derivatives), toluene (45 mL) , and triethylamine (20 mmol, 2.8 mL) . After refluxing the reaction mixture overnight (about 18 hours), the crude product was evacuated and dissolved in DCM. After adding concentrated hydrochloric acid (0.4 mL) , the mixture was washed by water (50 mL) and dried over anhydrous Na2SC . The organic solvent was removed to give the phthalimido-protected amino acid. Phthalimido-protected amino acid (10 mmol) , thionyl chloride (25 mmol) and several drops of DMF were added in toluene at 80 C for 3 hours. After the reaction, the excess of thionyl chloride was removed in vacuo, and the crude acid chloride was added to a vigorously stirring solution of 2,3,5,6- tetrafluoro-4- (trifluoromethlyl) aniline (10 mmol) in toluene (8 mL) . The reaction mixture was stirred for 12 hours under reflux, and then stirred at room temperature for 0.5 hours. The product mixture was concentrated in vacuo and was recrystallized from ethyl acetate/hexane to provide the amide. (S) -2-Phthalimido-Zi- (2,3,5, 6-tetrafluoro-4- ( rifluoromethy1) henyl) ropanamide (1) NMR (600 MHz, CDC13) delta 8.39 (br s, 1H) , 7.87-7.84 (m, 2H) , 7.78-7.75 (m, 2H) , 5.15 (q, J = 7.2 Hz, 1H) , 1.79 (d, J= 7.2 Hz, 3H) ; 13C NMR (150 MHz, CDC13) 8167.7, 167.5, 134.6, 131.4, 123.8, 49.9, 15.5; HRMS (ESI-TOF) Calcd for C18HioF7 203 [M+H] + : 435.0574; found: 435.0574. The ee value was determined by HPLC analysis on a Chiralcel OD-H column (20% isopropanol/hexanes , 0.5 mL/min) with tr 30.5 min (major), 56.1 min (minor): 97% ee. (S) -3-Phenyl-2-phthalimxdo-N- (2,3,5, 6-tetrafluoro-4- (trifluoromethyl) henyl) propanamxde (2) 1H NMR (400 MHz , CDC13) delta 8.50 (br s, 1H) , 7.83-7.78 (m, 2H) , 7.75-7.71 (m, 2H) , 7.23-7.13 (m, 5H) , 5.34 (dd, Ji = 6.4 Hz, J2 = 10.4 Hz, 1H) , 3.64 (ABqd, Jx = 6.4 Hz, J2 = 14.2 Hz, 1H) , 3.58 (ABqd, Ji = 10.4 Hz, J2 = 14.2 Hz, 1H) ; 13C NMR (100 MHz, CDC13) 5168.0, 166.6, 135.4, 134.7, 131.0, 128.9, 128.8, 127.4, 123.8, 56.6, 35.3; HRMS (ESI-TOF) Calcd for C24Hi4F7 203 [M+H]+: 511.0887; found: 511.0883. (S) -2 , 6-Bis (phthalimido) -N- (2,3,5, 6-tetrafluoro-4- (trifluoromethyl) phenyl) hexanamide (5a) NMR (400 MHz, CDCI3) delta 8.68 (br s, 1H) , 7.91-7.87 (m, 2H) , 7.82-7.77 (m, 4H) , 7.73-7.70 (m, 2H) , 5.04 (dd, Jx = 6.4 Hz, J2 = 9.6 Hz, 1H) , 3.70 (t, J= 7.0 Hz, 2H) , 2.49-2.32 (m, 2H) , 1.82-1.74 (m, 2H) , 1.50- 1.38 (m, 2H) ; 13C NMR (150 MHz, CDC13) 5168.5, 168.2, 166.8, 134.7, 134.0, 131.9, 131.3, 124.0, 123.2, 55.3, 36.9, 28.6, 27.5, 23.2; HRMS (ESI-TOF) Calcd for C29Hi9F7N305 [M+H]+: 622.1207; found: 622.1203. (S) -2-Phthalimido-N- (2,3,5, 6-tetrafluoro-4- (trifluoromethyl) phenyl) butanamide (5b) NMR (400 MHz, CDC13) delta 8.68 (br s, 1H) , 7.95-7.91 (m, 2H) , 7.83-7.79 (m, 2H) , 5.00 (dd, Jx = 6.8 Hz, J2 = 9.6 Hz, 1H) , 2.42-2.25 (m, 2H) , 1.02 (t, J= 7.4 Hz, 3H) ; 13C NMR (100 MHz, CDC13) delta 168.3, 167.1, 134.8, 131.2, 123.9, 57.1, 22.9, 10.6; HRMS (ESI-TOF) Calcd for C19Hi2F7N203 [M+H] +: 449.0731; found: 449.0733. l-Phthalimido-tf- (2,3,5, 6-tetrafluoro-4- (trifluoromethyl) phenyl) cyclobutaneoarboxamide (5c) JH NMR (400 MHz, CDC13) delta 8.23 (br s, 1H) , 7.89-7.85 (m, 2H) , 7.79-7.76 (m, 2H) , 3.14-3.09 (m, 2H) , 2.84- 2.75 (m, 2H) , 2.19-2.00 (m, 2H) ; 13C NMR (100 MHz, CDCI3) 8169.1, 168.0, 134.6, 131.5, 123.5, 60.8, 31.6, 17.3; HRMS (ESI-TOF) Calcd for C2oHi2F7N203 [M+H]+: 461.0731; found: 461.0727. 1-Phthalimido-W- (2,3,5, 6-tetrafluoro-4- (trifluoromethyl) henyl) cyclopropanecarboxamide (5d) H NMR (600 MHz, CDC13) delta 7.94-7.91 (m, 2H) , 7.84-7. (m, 2H) , 7.50 (br s, 1H) , 1.97 (dd, Jx = 5.4 Hz, J2 9.0 Hz, 2H) , 1.50 (dd, Ji = 5.4 Hz, J2 = 9.0 Hz, 2H) 13C NMR (150 MHz, CDCI3) 6168.0, 135.0, 131.2, 124.0 33.5, 17.3; HRMS (ESI-TOF) Calcd for Ci9H9F7N203Na [M+Na]+: 469.0394; found: 469.0389. 3,3, 3-Trideuterio-2-methyl-W~ (2,3,5, 6-tetrafluoro-4- (trifluoromethyl) henyl) ropionamide (21) NMR (600 MHz, CDCI3) delta 7.00 (br s, 1H) , 2.67 (q, J = 7.2 Hz, 1H) , 1.31 (d, J= 7.2 Hz, 3H) ; 13C NMR (150 MHz, CDCI3) 5174.6, 35.6, 19.3; HRMS (ESI-TOF) Calcd for CuH6D3F7N0 [M+H]+: 307.0752; found: 307.0754. Me N O Me L10 2 , 5-Dimethyl-3 , 4-dihydro-2H-pyrano [2 , 3-£>] quinoline (L10) L10 was synthesized according to the literature procedure [Zhang et al., Org. Lett. 9:3651-3653 (2007)]. NMR (400 MHz, CDC13) delta 7.89 (d, J = 8.4 Hz, 1H) , 7.83 (d, J= 8.4 Hz, 1H) , 7.59- 7.55 (m, 1H), 7.39-7.35 (m, 1H) , 4.42-4.35 (m, 1H) , 3.04-2.98 (m, 1H) , 2.92-2.83 (m, 1H) , 2.56 (s, 3H) , 2.18-2.12 (m, 1H) , 1.90-1.76 (m, 1H) , 1.52 (d, J = 6.4 Hz, 3H) . 9-Fluoro-2 ,5-dimethyl-3 , 4-dihydro-2H-pyrano [2 , 3- b]quinoline (Lll) Lll was synthesized according to the literature procedure [Zhang et al., Org. Lett. 9:3651-3653 (2007)]. H NMR (400 MHz, CDC13) delta 7.69- 7.61 (m, 1H) , 7.31-7.25 (m, 2H) , 4.44-4.36 (m, 1H) , 3.04-2.98 (m, 1H) , 2...

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 13194 - 13197
[2]Journal of the American Chemical Society,2015,vol. 137,p. 4618 - 4621
[3]Patent: WO2015/131100,2015,A1 .Location in patent: Page/Page column 80-85

35
[ 651-83-2 ]
[ 175277-11-9 ]
3-(tert-butyl)-1-methyl-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-1H-pyrazole-5-carboxamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 2501 - 2504
Angew. Chem.,2015,vol. 127,p. 2531 - 2534,4

36
[ 195447-83-7 ]
[ 651-83-2 ]
2-ethyl-8-fluoro-4,4-dimethyl-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-4,5-dihydro-2H-benzo[e]indazole-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / 1-methyl-pyrrolidin-2-one / 16 h / 90 °C 2: silver(l) oxide; tetrakis(acetonitrile)palladium bistriflate / acetic acid / 24 h / 120 °C

Reference： [1]Yang, Weibo; Ye, Shengqing; Fanning, Dewey; Coon, Timothy; Schmidt, Yvonne; Krenitsky, Paul; Stamos, Dean; Yu, Jin-Quan [Angewandte Chemie - International Edition, 2015, vol. 54, # 8, p. 2501 - 2504][Angew. Chem., 2015, vol. 127, # 8, p. 2531 - 2534,4]

37
[ 195447-83-7 ]
[ 651-83-2 ]
3-(tert-butyl)-1-ethyl-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-1H-pyrazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 90℃; for 16h;

Reference： [1]Yang, Weibo; Ye, Shengqing; Fanning, Dewey; Coon, Timothy; Schmidt, Yvonne; Krenitsky, Paul; Stamos, Dean; Yu, Jin-Quan [Angewandte Chemie - International Edition, 2015, vol. 54, # 8, p. 2501 - 2504][Angew. Chem., 2015, vol. 127, # 8, p. 2531 - 2534,4]

38
[ 88-13-1 ]
[ 651-83-2 ]
[ 1465827-64-8 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100℃; for 18h;	Intermediate 4-9-A. W-(2,3,5,6-Tetrafluoro-4-(trifluoromethyl)phenyl)thiophene-3- carboxamideA mixture of thiophene-3-carboxylic acid (CAS 88-13-1 , 2.24 g, 17.5 mmol), T3P (2 M in DMF, 12.5 mL, 25 mmol), DIPEA (6.2 mL, 35.5 mmol) and 2,3,5,6-tetrafluoro-4- (trifluoromethyl)aniline (4.45 g, 19.1 mmol) was stirred at 100 C for 18 h, and then cooled to room temperature. The reaction mixture was then poured into sat. aq. NH4CI, and then stirred for 0.5 h. Resulting precipitate was collected by filtration. The precipitate was then triturated with CH2CI2 (ca. 60 mL). The solid was collected by filtration, rinsed with CH2CI2, to afford the title compound. MS (ESI+) m/z 344.0 (M+H).

Reference： [1]Organic Letters,2016,vol. 18,p. 3310 - 3313
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 2552 - 2570
[3]Patent: WO2016/1876,2016,A1 .Location in patent: Page/Page column 79

39
[ 651-83-2 ]
[ 28697-07-6 ]
C₂₁H₁₇F₇N₂O₃ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 4748 - 4752

40
[ 651-83-2 ]
5-tert-butyl-2-[(2,4,6-trimethylphenyl)methyl]pyrazole-3-carboxylic acid [ No CAS ]
5-tert-butyl-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-2-[(2,4,6-trimethylphenyl)methyl]pyrazole-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.4%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 80℃; for 16h;	In a 20 mL sealed flask containing 5-tert-butyl-2-[(2,4,6-trimethylphenyl)methyl]pyrazole-3-carboxylic acid 1 (500. mg, 1.66 mmol) was added N-methylpyrrolidinone (5.000 mL) and diisopropylamine (537.7 mg, 724.7 muL, 4.160 mmol) followed by a propylphosphonic anhydride solution (2.118 mL of 50% w/v, 3.328 mmol) and <strong>[651-83-2]2,3,5,6-tetrafluoro-4-(trifluoromethyl)aniline</strong> (426.5 mg, 1.830 mmol) and the resulting mixture was stirred at 80 C. for 16 hours. The material was diluted with ethyl acetate (10 mL), washed with water and the organic layer was extracted. The organic layer was washed twice with a saturated aqueous solution of sodium bicarbonate, followed by brine. The material was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The resulting crude material was adsorbed to celite and purified by silica gel column chromatography ((40 g) using a gradient of 0 to 50% ethyl acetate) to afford 5-tert-butyl-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-2-[(2,4,6-trimethylphenyl)methyl]pyrazole-3-carboxamide (748 mg, 1.44 mmol, 86.4%). ESI-MS m/z calc. 515.1808. found 516.2 (M+1)+; Retention time: 2.58 minutes. 1H NMR (400 MHz, DMSO) delta 10.92 (s, 1H), 7.01 (s, 1H), 6.83 (s, 2H), 5.64 (s, 2H), 2.27 (s, 6H), 2.21 (s, 3H), 1.20 (s, 9H).

Reference： [1]Patent: US2016/95858,2016,A1 .Location in patent: Paragraph 4440; 4441

41
[ 651-83-2 ]
[ 700-17-4 ]
2-((4-amino-2,3,5,6-tetrafluorophenyl)ethynyl)-3,5,6-trifluoro-4-(trifluoromethyl)aniline [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2016,vol. 188,p. 85 - 98

42
[ 651-83-2 ]
[ 1991-43-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With iodine; iodic acid; In 1,4-dioxane; water; for 4h;Reflux;	To a stirred solution of aniline 7 (3.0 g, 18 mmol) in dioxane (70 mL), we added fine-ground I2 (2.3 g, 9 mmol) and a solution of HIO3 (3.2 g, 18 mmol) in H2O (12 mL). The reaction mixture was refluxed for 4 h, cooled to r.t., poured into H2O (50 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with a saturated water solution of Na2SO3 (50 mL) solution several times, then with H2O (100 mL) and dried (MgSO4). After evaporation of the solvent in vacuo, the crude product was recrystallized from hexane to obtain the title product (5.0 g, 96 %) as light brown solid; m.p. 73.4-74.0 C (lit. data: 76.9-77.7C [36]); [Found: C, 24.38; H, 0.75; N, 4.44. C6H2F4IN requires C, 24.77; H, 0.69; N 4.81 %]; numax (KBr): 3483, 3389, 1655, 1491, 1173, 1101, 920, 802 cm-1; 1H NMR (500.13 MHz, CDCl3): delta=4.12 (br s, 2H, NH2); 13C NMR (125.76 MHz, CDCl3): delta=146.8 (dm, 1JC3,F=240.9, 2JC3,F=11.8 Hz, C3), 136.0 (ddt, 1JC2,F=242.0, 2JC2,F=17.3 Hz, C2), 126.8 (tt, 2JC1,F=14.3, 3JC1,F=3.5 Hz, C1), 55.1 (t, 2JC4,F=28.1 Hz, C4); 19F NMR (282.37 MHz, CDCl3): delta=-122.4 (dm, 2F, JF3,F2?16 Hz, F3), -157.6 (dm, 2F, JF2,F3?16 Hz, F2); HRMS (EI): +, found 290.9166. C6H2F4IN requires 290.9168.

Reference： [1]Journal of Fluorine Chemistry,2016,vol. 188,p. 85 - 98

43
[ 651-83-2 ]
[ 700-17-4 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sulfuric acid; at 150℃; for 2h;	Aniline 7 (15 g, 64 mmol) in concentrated H2SO4 (50 mL) was stirred with a condenser at 150 C for 2 h. Then, H2O (100 mL) was added into the reaction flask, and the reaction product was separated by steam distillation. The distillate was extracted with CH2Cl2 (3×50 mL), washed with H2O (50 mL) and dried (MgSO4). After evaporation of the solvent in vacuo, the title product (7 g, 66 %) was obtained as light yellow liquid (the 1H and 19F NMR spectra closely match the literature data [36]. numax (KBr): 3501, 3414 (NH2), 1664, 1618, 1524, 1400, 1269, 1178, 1090, 887, 804, 716 cm-1; 1H NMR (300.13 MHz, CDCl3): delta=6.36 (tt, 1H, JH,F3=10.5; JH,F2=7.3Hz, Har), 4.03 (br s, 2H, NH2); 13C NMR (100.62 MHz, CDCl3): delta=146.2 (dm, 1JC3,F=243.4, 2JC3,F=12.6Hz, C3), 136.3 (ddt, 1JC2,F=238.1, 2JC2,F=16.2Hz, C2), 126.7 (tt, 2JC1,F=14.3, 3JC1,F=4.3Hz, C1), 93.0 (t, 2JC4,F=23.2Hz, C4); 19F NMR (282.37 MHz, CDCl3): delta=-142.9 (m, 2F, JF3,F2=24, JF3,H=10Hz, F3), -163.3 (m, 2F, JF2,F3=24, JF2,H=7Hz, F2); HRMS (EI): +, found 165.0205. C6H3F4N requires 165.0196.

Reference： [1]Journal of Fluorine Chemistry,2016,vol. 188,p. 85 - 98

44
[ 651-83-2 ]
2-phenyl-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)thiophene-3-carboxamide [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 3310 - 3313
[2]Organic Letters,2016,vol. 18,p. 3310 - 3313

45
[ 651-83-2 ]
4-bromo-2-phenyl-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)thiophene-3-carboxamide [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 3310 - 3313
[2]Organic Letters,2016,vol. 18,p. 3310 - 3313

46
[ 488-93-7 ]
[ 651-83-2 ]
N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)furan-3-carboxamide [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 3310 - 3313

47
[ 55312-97-5 ]
[ 651-83-2 ]
2-(2,5-dimethylphenyl)-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; for 20h;Reflux;	Aside from analyses of NMR spectra, the structures of the meta-C-H alkylation products were also confirmed by the comparison with two authentic samples prepared from commercially available 2,5- dimethylphenylacetic acid and 3 , 5-dimethylphenyl- acetic acid.

Reference： [1]Patent: WO2016/123361,2016,A1 .Location in patent: Page/Page column 94; 95

48
[ 42288-46-0 ]
[ 651-83-2 ]
2-(3,5-dimethylphenyl)-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; for 20h;Reflux;	Aside from analyses of NMR spectra, the structures of the meta-C-H alkylation products were also confirmed by the comparison with two authentic samples prepared from commercially available 2,5- dimethylphenylacetic acid and 3 , 5-dimethylphenyl- acetic acid.

Reference： [1]Patent: WO2016/123361,2016,A1 .Location in patent: Page/Page column 94; 95

49
[ 1914-65-4 ]
[ 651-83-2 ]
N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; ethyl acetate; at 80℃; for 16h;Sealed tube;	The carboxylic acid (2.0 mmol) and 2,3,5,6- tetrafluoro-4- (trifluoromethyl) aniline (2.2 mmol) were dissolved in 7.0 mL l-methyl-2-pyrrolidone (NMP) in a 35 mL pressure tube. 2.5 mL (4.2 mmol) of propylphosphonic anhydride solution (T3P, 50 wt. % in ethyl acetate) and 0.7 mL (4.0 mmol) of N,N- diisopropylethylamine (DIPEA) were then added using syringes. The tube was sealed with a Teflon screw cap and the mixture was stirred at 80C for 16 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate (15 mL) and water (10 mL) , and then the organic layer was separated, washed with brine (10 mL><3) and dried over anhydrous Na2S04. After filtration and evaporation, the resulting crude materials were passed through a short silica gel column with ethyl acetate/hexanes (1:1) as the eluent to remove the very polar compounds. The collected product fraction mixed with the residual 2,3,5,6- tetrafluoro-4- (trifluoromethyl) aniline was concentrated. The resulting solid mixture was recrystallized with ethyl acetate and hexanes to give the pure product. Use of T3P as a promoter for amide formation had been discussed in the previous literature [Ech-Chahad et al., Tetrahedron Letters 46, 5113-5115 (2005) ] . Substrates lu-x were prepared following this procedure. 1u N- [2 ,3,5, 6-tetrafluoro-4- ( rifluoromethyl) phenyl] - 1,2,3, 4-tetrahydronaphthalene-1-carboxamide NMR (600 MHz, CDC13) delta 7.30-7.20 (m, 4H) , 6.81 (br, 1H, N-H) , 3.95 (t, J = 5.4 Hz, 1H) , 2.95- 2.82 (m, 2H) , 2.42-2.35 (m, 1H) , 2.14-2.07 (m, 1H) , 1.94-1.85 (m, 2H) ; 13C NMR (150 MHz, CDC13) delta 173.09, 138.32, 132.74, 130.44, 130.05, 128.37, 126.91, 47.43, 29.19, 27.65, 20.39. HRMS (ESI-TOF) m/z Calcd for Ci8HiiF7 O_ [M-H]~ 390.0734, found 390.0752.

Reference： [1]Patent: WO2016/123361,2016,A1 .Location in patent: Page/Page column 43; 44

50
[ 55116-09-1 ]
[ 651-83-2 ]
2-(2-bromophenyl)-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;Inert atmosphere; Reflux;	The previous reported procedure [Wang et al., J. Am. Chem. Soc. 135, 10326-10329 (2013)] was followed. Thus, 2, 3, 5, 6-tetrafluoro-4- (trifluoromethyl) aniline (6.0 mmol) and an acid chloride (5.0 mmol), prepared from the corresponding carboxylic acid and oxalyl chloride (or thionyl chloride for substrate Compounds lr, Is and It) , were dissolved in toluene (10.0 mL) in a 50 mL round- bottom flask. The mixture was stirred and refluxed under N2 for 24 hours. After cooling to room temperature, the product mixture was concentrated in vacuo and was recrystallized from ethyl acetate/hexanes to give the pure amide substrate. Phenylacetic amide Compounds la-c, le-g, li, 1j , lo and lp had been synthesized and characterized before [Wang et al. , J. Am. Chem. Soc. 135, 10326-10329 (2013) ] 2- (2-Bromop enyl) -N- [2 , 3 , 5 , 6-tetrafluoro-4- (trifluororaethyl) phenyl] acetamide 1R NMR (600 MHz, acetone-d6) delta 9.63 (br, 1H, N-H) , 7.63 (d, J = 8.0 Hz, 1H) , 7.49 (d, J = 8.0 Hz, 1H) , 7.38 (t, J = 8.0 Hz, 1H) , 7.25 (t, J = 8.0 Hz, 1H) , 4.07 (s, 2H) ; 13C NMR (150 MHz, acetone-d6) delta 168.38, 135.72, 133.48, 133.06, 130.00, 128.63, 125.68, 43.45. HRMS (ESI-TOF) m/z Calcd for CisHgBrFT O" [M-H]~ 427.9526, found 427.9528.

Reference： [1]Patent: WO2016/123361,2016,A1 .Location in patent: Page/Page column 38; 39

51
[ 609-71-2 ]
[ 651-83-2 ]
2-hydroxy-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)nicotinamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 14876 - 14879

52
[ 651-83-2 ]
[ 38076-80-1 ]
5-chloro-2-hydroxy-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)nicotinamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 14876 - 14879

53
[ 651-83-2 ]
C₆H₄FNO₃ [ No CAS ]
5-fluoro-2-hydroxy-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)nicotinamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 14876 - 14879

54
[ 651-83-2 ]
[ 363-80-4 ]

Reference： [1]Tetrahedron,2017,vol. 73,p. 1219 - 1229

55
[ 828-51-3 ]
[ 651-83-2 ]
N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)adamantane-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		1-adamantane carboxylicacid(40.8 mmol, 7.4 g) was added to 16 ml of a solution of ,Then, 3 drops of DMF were added dropwise and refluxed at 80 C for 2 hours. The reaction solution was spin-Remove excess thionyl chloride. The residue was dissolved in 50 mL of anhydrous tolueneTo a solution of 2,3,5,6_ tetrafluoro-4- (trifluoromethyl) aniline(10 mm0, 2.4 g),After 12 hours at 120 C, the reaction solvent was dried,Recrystallization from petroleum etherN- (2,3,5,6-tetrafluoro-4- (trifluoromethyl) phenyl) -1-adamantane formamide,White solid in 73% yield.

Reference： [1]Patent: CN104693039,2016,B .Location in patent: Paragraph 0055-0057

56
[ 14670-94-1 ]
[ 651-83-2 ]
3,5-dimethyl-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-1-adamantane carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		S1 3,5-dimethyl adamantane-1 -carboxylic acid (28.8mmol, 6g) was added to 15mL thionyl chloride was dropwise into 3 drops of DMF, 2 hours, the reaction was refluxed at 80 C, by rotary evaporation Remove excess thionyl chloride.The residue was dissolved in 50 mL of anhydrous toluene, and 2,3,5,6-tetrafluoro-4- (trifluoromethyl) aniline (14 mmol, 3.4 g) was added and refluxed at 120 C for 12 hours.The reactionsolventwas driedand the crystals were recrystallized from petroleum ether to give 3,5-dimethyl-N- (2,3,5,6-tetrafluoro-4- (trifluoromethyl) phenyl) -1-adamantane Acarboxamide as a white solid, yield 64%

Reference： [1]Patent: CN104693039,2016,B .Location in patent: Paragraph 0042-0044

57
[ 651-83-2 ]
[ 407-25-0 ]
[ 793-93-1 ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 13092 - 13101

58
[ 20769-85-1 ]
[ 651-83-2 ]
C₁₁H₇BrF₇NO [ No CAS ]

Reference： [1]Organometallics,2019,vol. 38,p. 138 - 142
[2]Journal of the American Chemical Society,2018,vol. 140,p. 5599 - 5606

59
[ 75-15-0 ]
[ 651-83-2 ]
4,5,7-trifluoro-6-(trifluoromethyl)benzo[d]thiazole-2(3H)-thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 50℃; for 1h;Schlenk technique; Inert atmosphere;	General procedure: Carbon disulfide is extremely stench, flammable, oxidizing and toxic by inhalation, skin absorption, and ingestion. To a solution of aniline 1 (1.5mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (456mg, 3mmol) in toluene (5mL) in a Schlenk flask under argon was added CS2 (1mL). The reaction mixture was stirred at 50C for 1-25h. The mixture was allowed to cool to room temperature, and EtOAc (10mL) was added. The mixture was poured into 0.5M aqueous AcOH solution (50mL) and extracted with EtOAc (3×50mL). The combined organic solution was washed with H2O (50mL) and dried (MgSO4). After evaporation of the solvent in vacuo, the crude product was purified by porphyrization with hexane (10mL). Yellowish solution containing impurities was removed and solid was re-dried in vacuum to obtain the title product 2 4.2.2.1 4,5,7-Trifluoro-6-(trifluoromethyl)benzo[d]thiazole-2(3H)-thione (2a) Yellow solid; yield: 429?mg (99%); mp 183.4-184.4?C. IR (KBr): 3442, 3003, 2943, 2831, 2700, 1641, 1514, 1448, 1309, 1259, 1211, 1190, 1169, 1088, 1068, 924, 816, 779, 764, 694, 656, 646, 544, 438 cm-1. 1H NMR (300?MHz, CDCl3): 10.62 (br s, NH). 13C NMR (126?MHz, Acetone-d6): delta?=?192.7 (s, C2), 147.9 (ddm, 1J (C5,F5)?=?256.0?Hz, 2J (C5,F4)?=?11.4?Hz, C5), 147.6 (dm, 1J (C7,F7)?=?254.0?Hz, C7), 135.5 (m, C3a), 134.1 (ddd, 1J (C4,F4)?=?250.2?Hz, 2J (C4,F5)?=?16.9?Hz, 4J (C4,F7)?=?4.4?Hz C4), 122.4 (qm, 1J (CF3,F)?=?273.0?Hz, CF3), 115.2 (dm, 2J (C7a,F7)?=?25.4?Hz, C7a), 103.7 (m, C6). 19F NMR (282?MHz, Acetone-d6): delta = -53.8 (dd, J (CF3,F5)?=?22.7?Hz, J (CF3,F7)?=?21.1?Hz, 3?F, CF3), -114.0 (m, J (F5,CF3)?=?22.7?Hz, J (F5,F4)?=?15.6?Hz, J (F5,F7)?=?3.0?Hz, 1?F, F5), -133.6 (m, J (F7,CF3)?=?21.1?Hz, J (F7,F4)?=?20.1?Hz, J (F7,F5)?=?3.0?Hz, 1?F, F7), -152.7 (dd, J (F4,F7)?=?20.1?Hz, J (F4,F5)?=?15.6?Hz, 1?F, F4). HRMS (EI): m/z [M]+ calcd for C8H1F6NS2: 288.9449; found: 288.9446. Anal. Calcd for C8H1F6NS2: C, 33.22; H, 0.35; N, 4.83. Found: C, 33.41; H, 0.50; N, 5.23.

Reference： [1]Journal of Fluorine Chemistry,2018,vol. 212,p. 130 - 136

60
[ 651-83-2 ]
[ 65171-20-2 ]

Yield	Reaction Conditions	Operation in experiment
56%	With calcium hypochlorite; In neat (no solvent); for 0.5h;Milling;	General procedure: Fluorinated aniline (1g) and Ca(ClO)2 (1.2 equiv) were added to the zirconia reactor equipped with four zirconia milling balls (d=1cm). The mixture was shaken at 15 Hz for the time stated in the text. The residue was collected with dichloromethane, the organic solution was washed with water (3×100mL), dried over Na2SO4, SiO2 was added to the resulting solution and the solvent was removed under reduced pressure. Purification over a short pad of silica gel eluting with n-hexane afforded the desired azobenzene in a pure form.

Reference： [1]Journal of Fluorine Chemistry,2018,vol. 216,p. 124 - 127

61
[ 651-83-2 ]
[ 65-85-0 ]
[ 80588-64-3 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 2645 - 2649

62
[ 651-83-2 ]
[ 107-92-6 ]
[ 1407870-22-7 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: An acid chloride (1 equiv.), prepared from the corresponding carboxylic acid and oxalyl chloride, was added to a vigorously stirred solution of <strong>[651-83-2]2,3,5,6-tetrafluoro-4-(trifluoromethyl)aniline</strong> (ArFNH2) (1.1 equiv.) in toluene (1 M). The reaction mixture was stirred for 12 hours under reflux, and then cooled at room temperature. The product mixture was concentrated under vacuum and was recrystallized from ethyl acetate/hexane to give the desired amide. In the 13C NMR analysis, peaks that correspond to those of the polyfluoroarylamide auxiliary appeared as nearly invisible, complex sets of multiplets; they are omitted in the following spectroscopic analysis.1H NMR (600 MHz, CDCl3) delta 6.99 (br s, 1H), 2.47 (t, J=7.4 Hz, 2H), 1.83-1.76 (m, 2H), 1.04 (t, J=7.4 Hz, 3H).

Reference： [1]Patent: US2019/315710,2019,A1 .Location in patent: Paragraph 0139-0141

63
[ 651-83-2 ]
N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-P,P-diphenylphosphinicamide [ No CAS ]
C₂₈H₁₉F₇N₃O₂P [ No CAS ]

Reference： [1]Chemical Communications,2020,vol. 56,p. 1444 - 1447

64
[ 1211417-77-4 ]
[ 651-83-2 ]
(2-amino-3,4,6-trifluoro-5-(trifluoromethyl)phenyl)(1,3-dimethyl-1H-imidazol-3-ium-2-yl)dihydroborate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 4009 - 4016
Angew. Chem.,2020,vol. 132,p. 4038 - 4045,8

65
[ 651-83-2 ]
[ 40913-92-6 ]
4-(methylsulfonyl)-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	In toluene for 24h; Reflux;	2.1 General procedure for the preparation of benzamides 1a-1ac ^1-2 General procedure: Acid chloride (20 mol) was prepared from the corresponding carboxylic acid and oxalyl chloride. Acid chloride was added to a solution of 2,3,4,5,6-pentafluoroaniline (22 mmol) in toluene (50 mL). The reaction mixture was stirred for 24 h under reflux. After cooling to room temperature, the precipitate was filtered off, washed with water, and recrystallized from toluene or ethyl acetate/hexane to give the products 1 (the crude mixture was sometimes purified by flash chromatography if necessary).

Reference： [1]Wu, Peng; Cheng, Tai-Jin; Lin, Hai-Xia; Xu, Hui; Dai, Hui-Xiong [Tetrahedron Letters, 2020, vol. 61, # 28]

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