[ CAS No. 142808-15-9 ]

Name: 142808-15-9|4-Bromo-2-fluorobenzotrifluoride|98%
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Quality Control of [ 142808-15-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 142808-15-9 ]

Product Details of [ 142808-15-9 ]

CAS No. :	142808-15-9	MDL No. :	MFCD01075254
Formula :	C₇H₃BrF₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OEPBVXQEVBURGC-UHFFFAOYSA-N
M.W :	243.00	Pubchem ID :	2782904
Synonyms :

Calculated chemistry of [ 142808-15-9 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	39.1
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.23 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.27
Log Po/w (XLOGP3) :	3.6
Log Po/w (WLOGP) :	5.18
Log Po/w (MLOGP) :	4.51
Log Po/w (SILICOS-IT) :	3.95
Consensus Log Po/w :	3.9

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.92
Solubility :	0.0293 mg/ml ; 0.000121 mol/l
Class :	Soluble
Log S (Ali) :	-3.29
Solubility :	0.126 mg/ml ; 0.000517 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.42
Solubility :	0.00922 mg/ml ; 0.0000379 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.43

Safety of [ 142808-15-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 142808-15-9 ]

* 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 [ 142808-15-9 ]

[ 142808-15-9 ] Synthesis Path-Downstream 1~69

1
[ 142808-15-9 ]
[ 214360-73-3 ]
3'-fluoro-4'-(trifluoromethyl)-4-biphenylamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4939 - 4952

2
[ 142808-15-9 ]
[ 304876-18-4 ]
[ 304875-19-2 ]

Yield	Reaction Conditions	Operation in experiment
30%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene;Heating / reflux;	5-[4-Fluoro-3-(trifluoromethyl)phenyl]spiro[cyclohexane-1,3-[3H]indol]-2(1H)-one was prepared from (2'-oxo-2,3-dihydrospiro[cyclohexane-1,3'-[3H]indol]-5'-yl)boronic acid (2.5 g, 10 mmol) and 5-bromo-2-fluoro-trifluoromethylbenzene (2 g, 8 mmol) as described for Example 5, to afford the title compound (0.87 g, 30%) as a solid: mp. 222 C.; 1H NMR (DMSO-d6) delta 1.5-1.8 (m, 8 H), 1.8-2.0 (m, 2 H), 6.92 (d, 1 H, J=8.13 Hz), 7.51 (dd, 1 H, J=8.13, 1.76 Hz), 7.55 (dd, 1 H, J=10.54, 9.01 Hz) 7.72 (d, 1 H, J=1.76 Hz), 7.90 (dd, 1 H, J=7.03, 2.20 Hz), 7.98 (m, 1 H) and 10.39 (s, 1 H); MS (EI) m/z 363 (M+).

Reference： [1]Patent: US6355648,2002,B1 .Location in patent: Page column 58

3
[ 142808-15-9 ]
[ 57260-71-6 ]
[ 847547-12-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride;tris-(dibenzylideneacetone)dipalladium(0); at 100℃; for 5h;	Step 1; EPO <DP n="50"/> 4-(3-Fluoro-4-trifluoromethyl-phenyl)-piperazine-l-carboxylic acid tert-buty ester:; rert-butyl-1- piperazine-carboxylate (740 mg, 3.05 mmol) and 4-bromo-2-fluoro-l-trifluoromethyl -benzene (530 mg. 2.85 mmol) were dissolved in anhydrous toluene (6 mL, degassed). In a separate, septum-equipped vial were placed tri(dibenzylideneacetone)dipalladium (0) (152 mg, 0.17 mmol), l,3-bis(2,6-di-/- propylphenyl)imidazolium chloride (283 mg, 0.67 mmol) and sodium ;-butoxide (400 mg, 4.2 mmol). This "catalytic" vial was equipped with a magnetic stirbar and flushed with dry nitrogen. The reactant solution was next transferred to the "catalytic" vial and the mixture was stirred at 100 0C for 5 hours. After this period the mixture was combined with 2O mL of hexane/EtOAc (2:1) and was passed through a pad of Celite. The resulting filtrate was concentrated and purified using silica gel chromatography (0-20% EtOAc/Hexane) to yield 853 mg (86 %) of 4-(3-Fluoro-4-trifluoromethyl-phenyl)-piperazine-l-carboxylic acid tot-butyl ester as a yellow residue. 1H NMR (400MHz, CDCl3) delta 7.44-7.40 (m, IH), 6.65-6.58 (m, 2H), 3.59-3.56 (m, 4H), 3.27-3.25 (m, 4H), 1.49 (s, 9H).

Reference： [1]Patent: WO2006/55187,2006,A1 .Location in patent: Page/Page column 48-49

4
[ 142808-15-9 ]
[ 73183-34-3 ]
[ 445303-67-3 ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium acetate;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 100℃; for 12h;Inert atmosphere;	To a stirred solution of 4-bromo-2-fIuoro-1-(trifluoromethyl)benzene (5 g, 20.57 mmol) in 1,4- dioxane (400 mL), bis(pinacolato)diboron (5.2 g, 20.57 mmol) was added and deoxygenated twice. Potassium acetate (6.05 g, 61.72 mmol), PdCI2(PPh3)2 (0.43 g, 0.61 mmol) were added to it and again deoxygenated. The reaction was heated to 100C for 12 h. The reaction mixture was filtered through celite bed and evaporated to dryness. It was taken in ethyl acetate (200 mL) and was washed with water (2 x 100 mL). The final organic layer was dried over anhydrous magnesium sulfate and evaporated to dryness to afford crude compound, which was purified through column chromatography (silica: 100-20 mesh, eluent: 5% ethyl acetate in hexane) to afford compound (4 g, 67%).
61%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80℃; for 10h;microwave irradiation;	4-Bromo-2-fluoro-1-(trifluoromethyl)benzene (5.08 g, 20.91 mmol) was dissolved in DMSO (40 mL), then 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (6.16 g, 24.25 mmol), PdCl2 (dppf) (0.756 g, 1.05 mmol) and potassium acetate (4.10 g, 41.81 mmol) were added and the mixture was heated in an oil bath at 80 C. for 10 h. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried with Na2SO4 and evaporated. The residue was purified by automated flash chromatography on a Biotage KP-SIL 340 g column. A gradient from 0% to 20% of EtOAc in heptane over 10 CV was used as mobile phase. 2-(3-Fluoro-4-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane (3.72 g, 61%) was isolated.
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dichloromethane; N,N-dimethyl-formamide; at 80℃; for 2 - 2.5h;Product distribution / selectivity;	a) 6-[3-Fluoro-4-(trifluoromethyl)phenyl]-8-nitro-3,4-dihydro-2(1 H)-quinolinoneTo a stirred solution of <strong>[142808-15-9]4-bromo-2-fluoro-1-(trifluoromethyl)benzene</strong> (1.0 g, 4.1 mmol), bis(pinacolato)diboron (1.1 g, 4.3 mmol) and potassium acetate (1.2 g, 122 mmol) in dimethylformamide (50 mL) was added [1 ,1'- bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane adduct (81 mg, 0.11 mmol). After purging with nitrogen, the reaction was heated to 80 0C and EPO <DP n="89"/>stirred for 2 h. 6-bromo-8-nitro-3,4-dihydro-2(1 H)-quinolinone (example 77a, 1.0 g, 3.7 mmol), cesium fluoride (1.3 g, 8.4 mmol), and tetrakis(triphenylphosphine)palladium (0) (130 mg, 0.11 mmol) were added and the reaction stirred at 100 0C for 18 h. After cooling to room temperature, the reaction was evaporated to dryness under vacuum. The residue was taken up in ethyl acetate, filtered to remove insolubles, washed with 1 M aq hydrochloric acid, brine, dried (MgSO4), filtered and concentrated under vacuum. Purification by flash chromatography on silica gel (3% ethyl acetate/dichloromethane) gave the title compound (0.77 g, 59%) as a yellow solid. MS (ES) m/e 355.0 (M + H)+.; +/- 6-f3-Fluoro-4-(trifluoromethvnphenyl1-3-hyclroxy-3.4-dihvdro-2(1 H)-quinolinone 4-Bromo-2-fluoro-1-(trifluoromethyl)benzene (0.091 mL, 0.375 mmol), bis(pinacolato)diboror) (0.10 g, 0.394 mmol), potassium acetate (0.11 g, 1.12 mmol), dichloro[1 ,1 '-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.020 g, 0.027 mmol) in DMF (2.0 mL) were heated to 800C under nitrogen for 2.5 hours. After the reaction was cooled, dichloro[1 ,1'- bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.020 g, 0.027 mmol) was added followed by addition of + 6-bromo-3-hydroxy-3,4-dihydro- 2(1 H)-quinolinone (example 85b, 0.095 g, 0.392 mmol) and 2M Na2CO3 in water (0.98 mL). The reaction was heated to 800C. After 12 hours the reaction mixture was cooled and diluted with ethyl acetate, then washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude reaction mixture was purified using reverse-phase preparative HPLC (10% CH3CN/H2O to 100% CH3CN/H2O with 0.1% TFA) to give the title compound as a solid. 1H NMR (400MHz, D6-DMSO) delta 10.34 (bs, 1 H), 7.79 (m, 2H), 7.69 (m, 2H), 7.59 (d, J = 8.6Hz, 1 H), 6.96 (d, J = 8.3 Hz, 1 H), 5.58 (bs, 1 H), 4.18 (m, 1 H), 3.13 (dd, 1 H), 2.93 (dd, 1 H).

	With potassium acetate;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 100℃; for 4.5h;	PREPARATION 32 2-[3-fluoro-4-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane A solution of <strong>[142808-15-9]4-bromo-2-fluoro-1-(trifluoromethyl)benzene</strong> (20.57 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane (22.62 mmol), potassium acetate (61.70 mmol), and dichlorobis(triphenylphosphine)palladium(II) (0.822 mmol) in dioxane (200 mL) was heated at 100 C. for 4.5 h. The reaction mixture was cooled, dissolved into ethyl acetate (500 mL), and washed with water (3*200 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to provide the crude title product.
	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane;Inert atmosphere;	Example 80A2-[3-Fluoro-4-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane A mixture of 25 g (99.8 mmol) of <strong>[142808-15-9]4-bromo-2-fluoro-1-(trifluoromethyl)benzene</strong> in 500 ml of dioxane was admixed under argon at RT with 27.8 g (109.8 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis-1,3,2-dioxaborolane, 2.91 g (3.99 mmol) of 1,1-bis(diphenylphosphine)-ferrocenedichloropalladium(II) dichlormethane complex and with 29.38 g (299.4 mmol) of potassium acetate. The reaction mixture was stirred below 100 C. for several hours until conversion was substantially complete. The mixture was filtered through Celite and admixed with water. After addition of ethyl acetate and phase separation, the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product is purified by flash chromatography (silica gel-60, eluent: cyclohexane/ethyl acetate 3:1). This gave 18.22 g of crude product in 73% purity (LC-MS), which was reacted without any further purification steps.1H NMR (400 MHz, DMSO-d6): delta=7.82 (dd, 1H), 7.67 (d, 1H), 7.59 (d, 1H), 1.32 (s, 12H).
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110℃; for 0.166667h;Microwave irradiation;	General procedure: To 2 mL of 1,4-dioxane in microwave reaction vessel were added bromobenzene (0.20 g, 1.27 mmol), bis(pinacolato)diboron (0.36 g, 1.40 mmol), potassium acetate (0.38 g, 3.8 mmol), and PdCl2(dppf) (0.028 g, 0.038 mmol). The reaction mixture was heated to 110 C by microwave irradiation at power 100 W for 10 min. After solvent was removed under reduced pressure, the residue was purified by dry column vacuum chromatography (DCVC) using dichloromethane (DCM) as eluent provided the 0.16 g in 62 % yield;

Reference： [1]Patent: WO2010/127856,2010,A1 .Location in patent: Page/Page column 89
[2]Patent: US2010/261755,2010,A1 .Location in patent: Page/Page column 31
[3]Patent: WO2006/113432,2006,A2 .Location in patent: Page/Page column 87-88; 100
[4]Patent: US2007/142460,2007,A1 .Location in patent: Page/Page column 17
[5]Patent: US2011/21489,2011,A1 .Location in patent: Page/Page column 38
[6]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2513 - 2517

5
[ 142808-15-9 ]
[ 819058-34-9 ]
[ 858105-76-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dichloromethane; water; N,N-dimethyl-formamide; at 100℃; for 18h;	a) S.S'-Difluoro-^-ttrifluoromethylH-biphenylamineTo a stirred solution of 2-fluoro-4-iodoaniline (7.0 g, 29.5 mmol), bis(pinacolato)diboron (9.8 g, 38.6 mmol) and potassium acetate (8.7 g, 88.6 mmol) in dimethylformamide (150 ml_) was added [1 ,1 '- bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane adduct (0.66 g, 0.9 mmol). After purging with nitrogen, the reaction was heated to 80 0C and stirred for 4 h. 4-Bromo-2-fluoro-1-(trifluoromethyl)benzene (7.2 g, 29.6 mmol), potassium carbonate (10.2 g, 73.8 mmol), water (20 ml_) and [1 ,1'- bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane adduct (0.66 g, 0.9 mMol) were added and the reaction stirred at 100 0C for 18 h. After cooling to room temperature, the reaction was evaporated to dryness under vacuum. The residue was taken up in ethyl acetate, filtered to remove insolubles, washed with water, brine, dried (Na2SO4), filtered and concentrated under vacuum. Purification by flash chromatography on silica gel (20% ethyl acetate/hexanes), trituration with hexane, filtration and drying under vacuum gave the title compound (4.93 g, 61 %) as a white solid: MS (ES) m/e 274.0 (M + H)+.

Reference： [1]Patent: WO2006/113432,2006,A2 .Location in patent: Page/Page column 66

6
[ 142808-15-9 ]
3α-[2-propoxy-4-(trifluoromethyl)phenoxy]-8-azabicyclo[3.2.1]octane [ No CAS ]
3α-[2-n-propoxy-4-(trifluoromethyl)phenoxy]-8-[3-fluoro-4-(trifluoromethyl)phenyl]-8-azabicyclo[3.2.1]octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.54 g	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos; In toluene;Inert atmosphere; Reflux;	0.4 g of t-butoxysodium, 13.7 mg of Pd2(dba)3, and 17.7 mg of 2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)biphenyl were added to 11 ml of toluene solution containing 1 g of the free form of the compound (F) obtained above and 0.73 g of <strong>[142808-15-9]4-bromo-2-fluorobenzotrifluoride</strong> and the entire mixture was refluxed overnight under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The residue was purified by column chromatography (developing solution: mixed solvent of n-hexane and ethyl acetate) to obtain 0.54 g of the target compound. Viscous oil 1H-NMR(CDCl3, deltappm):1.08(t, 3H), 1.81-1.97(m, 4H), 2.04-2.23(m, 4H), 2.45(q, 2H), 3.97(t, 2H), 4.19(brs, 2H), 4.57(brt, 1H), 6.44-6.51(m, 2H), 6.76(d, 1H), 7.13(s, 1H), 7.16(d, 1H), 7.38(t, 1H)

Reference： [1]Patent: WO2007/40282,2007,A1 .Location in patent: Page/Page column 28-29
[2]Patent: EP1932844,2015,B1 .Location in patent: Paragraph 0077

7
[ 142808-15-9 ]
[ 29632-74-4 ]
3,3'-difluoro-4'-(trifluoromethyl)-4-biphenylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		A solution of 2-fluoro-4-iodoaniline (14.8 mmol), bis(pinacolato)diboron (19.2 mmol), potassium acetate (44.3 mmol), and dichloro[1 ,1 '- bis(diphenylphosphino)ferrocene]palladium(ll)«dichloromethane adduct (0.45 mmol) in Lambda/,Lambda/-dimethylformamide (80 ml.) was heated at 80 0C for 2 h. The reaction mixture was cooled and was treated with <strong>[142808-15-9]4-bromo-2-fluorobenzotrifluoride</strong> (14.8 mmol), potassium carbonate (73.8 mmol), dichloro[1 ,1 '- bis(diphenylphosphino)ferrocene]palladium(ll)*dichloromethane adduct (0.45 mmol); and water (20 ml_). The reaction mixture was then heated at 100 0C for 18 h. The reaction mixture was cooled, concentrated in vacuo, dissolved in ethyl acetate (200 ml_), filtered, washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. Purification of the residue by flash chromatography (20% ethyl acetate/hexanes) provided the title product as a white solid (69%). ESMS [M+H]+: 274.2.

Reference： [1]Patent: WO2006/20358,2006,A2 .Location in patent: Page/Page column 38

8
[ 142808-15-9 ]
[ 1589-49-7 ]
[ 897956-21-7 ]

Yield	Reaction Conditions	Operation in experiment
		10.4 mmol of sodium hydride (60% dispersion in oil) are added in portions to a solution of 8.7 mmol of 3-methoxypropanol [1589-49-7] in 12 ml of dimethyl sulphoxide. The reaction mixture is stirred at room temperature for 30 minutes, and 1.3 g of sodium benzoate are added. The mixture is stirred at room temperature for 30 minutes, and 10.6 mmol of 4-bromo- 2-fluoro-1-trifluoromethylbenzene [1428808-15-9] are added in such a way that the internal temperature does not exceed 200C. After the addition is complete, the mixture is heated at EPO <DP n="55"/>65C for 15 hours. It is then cooled to room temperature. The reaction mixture is quenched with water/brine 1 :1 and extracted with dichloromethane (2x) - the combined organic phases are washed with brine, dried with sodium sulphate and evaporated. The title compound is identified by means of its Rf from the residue by flash chromatography (SiO2 60F).

Reference： [1]Patent: WO2006/95020,2006,A1 .Location in patent: Page/Page column 53-54

9
[ 142808-15-9 ]
[ 29632-74-4 ]
[ 858105-76-7 ]

Yield	Reaction Conditions	Operation in experiment
57%		PREPARATION 44 3,3'-difluoro-4'-(trifluoromethyl)-4-biphenylamine To a solution of 2-fluoro-4-iodoaniline (3.50 g, 14.8 mMol), bis(pinacolato)diboron (4.88 g, 19.2 mMol), and potassium acetate (4.35 g, 44.3 mMol) in N,N-dimethylformamide (80 mL) was added dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(ll)·dichloromethane adduct (0.33 g, 0.45 mMol). The reaction mixture was stirred at 80 C. for 4 h, at which point <strong>[142808-15-9]4-bromo-2-fluoro-1-(trifluoromethyl)benzene</strong> (3.6 g, 14.8 mMol), potassium carbonate (10.2 g, 73.8 mMol), water (20 mL), and additional dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II)·dichloromethane adduct (0.33 g, 0.45 mMol) were added. The reaction mixture was heated at 100 C. for 18 h and then cooled to room temperature. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate, filtered to remove insolubles, washed with brine, dried over sodium sulfate, and concentrated in vacuo. Purification of the residue by silica gel chromatography (20% ethyl acetate/hexanes), trituration with hexanes, filtration, and concentration in vacuo provided the title compound (2.30 g, 57%) as a white solid. ESMS [M+H]+: 274.2.

Reference： [1]Patent: US2007/142460,2007,A1 .Location in patent: Page/Page column 18

10
[ 142808-15-9 ]
[ 105-39-5 ]
[ 1255041-77-0 ]

Yield	Reaction Conditions	Operation in experiment
27%	With manganese;(2,2'-bipyridine)nickel(II) dibromide; trifluoroacetic acid; In N,N-dimethyl-formamide; at 65℃; for 1h;Inert atmosphere;	In a 50 mL two necked round bottom flask <strong>[142808-15-9]4-bromo-2-fluoro-1-(trifluoromethyl)benzene</strong> (0.5g, 2.05 mmol), ethyl chloroacetate (328 mg, 2.67 mmol), and dimethylformamide (4 mL) were charged. The system was degassed and re filled with argon followed by addition of Mn (225 mg, 4.1 mmol) and NiBr2. bipy (62 mg, 0.16 mmol). Finally TFA (4.1 muL) was added and the reaction mixture was degasified and refilled with argon. Then it was heated to 650C for one hour. TLC showed (10% ethyl acetate in hexane, Rf: 0.2) complete conversion of starting material. The reaction mixture was diluted with water (50 mL) and HCI (4N, 0.5 mL) and extracted with ethyl acetate (3 x 40 mL). The combined organic part was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford crude material which was purified by column chromatography (silica gel: 100-200 mesh, eluent: 10% ethyl acetate in hexane) to afford the pure compound (490 mg, 27%). 1H NMR (DMSOd6, 400 MHz): delta 7.54 (t, 1H), 7.15 (d, 2H), 4.16 (q, 2H), 3.64 (s, 2H), 1.26 (t, 3H).

Reference： [1]Patent: WO2010/127856,2010,A1 .Location in patent: Page/Page column 88

11
[ 142808-15-9 ]
[ 55305-43-6 ]
3-fluoro-4-(trifluoromethyl)benzonitrile [ No CAS ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 4217 - 4222

12
[ 123-75-1 ]
[ 142808-15-9 ]
[ 1396780-07-6 ]

Yield	Reaction Conditions	Operation in experiment
53%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 120℃;Sealed vessel;	Example 26 Synthesis of TRV 1 158[00166] TRV 1158 - phenyl(4-(3-(pyrrolidin- l -yl)-4-(trifluoromethy])phenyl)piperazin- l - yl)methanone[00167] Scheme for TRV 1 158DIPEA / N P[00168] A mixture of <strong>[142808-15-9]4-bromo-2-fluorobenzotrifluoride</strong> ( l .5 l l g, 6.2 mmol), pyrrolidine (0.62 mL, 7.46 mmol), DIPEA ( 1.6 mL, 9.33 mmol) and NMP (8 mL) were sealed in a tube and heated to 120 C overnight. The solution was cooled to room temperature and diluted with water and EtOAc. The layers were separated and the aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed successively with H2O, IN HCl(aq), saturated NaHC03(aq), H2O, and brine before drying with Na2SC>4. The mixture was filtered and concentrated to give a crude oil, which was purified via flash chromatography (5 % EtOAc / hexane) to give 0.9667 g (53 % yield) of desired product. This bromo-intermediate (0.5312 g, 1.8 mmol), benzoylpiperazine hydrochloride (0.4987 g, 2.2 mmol) and NaO/Bu (0.5189 g, 5.4 mmol) were charged to a flask which was subsequently purged and evacuated with argon (3 cycles). Toluene (5.4 mL) and NMP (3.2 mL) were then added and the solution was degassed for 30 minutes before added Pd2(dba)3 (0.033 g, 0.036 mmol) and BINAP (0.045 g, 0.072 mmol) all at once. The flask was then heated to 100 C overnight under argon. The mixture was cooled to room temperature and diluted with EtOAC before filtering through Celite. The organic layer was then washed successively with H20, IN HCl(aq), saturated NaHC03(aq), H2O, and brine before drying with Na2S04. The mixture was filtered and concentrated to give 0.5081 g of crude oil. The oil was purified via flash chromatography (45 % EtOAc / hexane) to give another crude oil that was slightly impure. This oil was crystallized from EtOAc (solvent) and hexane (anti-solvent) to give 0.101 g of white crystals of TRV 1158, phenyl(4-(3-(pyrrolidin-l -yl)-4- (trifluoromethyl)phenyl)piperazin- l-yl)methanone. NMR (500 MHz, DMSO) delta = 7.47-7.41 (m, 5H), 7.35 (d, J = 8.5 Hz, 1 H), 6.49 (dd, J = 8.5, 1.5 Hz, 1 H), 6.46 (m, 1 H), 3.72 (br s, 2H), 3.45 (br s, 2H), 3.30 (br s, 4H), 3.23-3.20 (m, 4H), 1.88- 1.83 (m, 4H).

Reference： [1]Patent: WO2012/119035,2012,A1 .Location in patent: Page/Page column 58-59

13
[ 142808-15-9 ]
[ 75-31-0 ]
[ 1396780-01-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 100℃;Sealed vessel;	Example 20 Synthesis of TRV 1 166[00146] TRV 1166 (4-(3-(isopropylamino)-4-(trifluoromethyl)phenyl)piperazin-l- yl)(phenyl)methanoneTRV 1166[00147] Scheme for TRV 1 166[00148] <strong>[142808-15-9]4-bromo-2-fluorobenzotrifluoride</strong> (0.5181 g, 2.13 mmol), isopropyl amine (0.22 mL, 2.56 mmol), DIPEA (0.56 mL, 3.2 mmol) and NMP (3 mL) were added to a tube. The tube was sealed and heated overnight at 100 C. After cooling, the reaction mixture was diluted with water and EtOAc. The aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed with H20, IN HCI (2x), saturated NaHC03, H20 and brine before drying with Na2S0 . The material was filtered and concentrated under reduced pressure to give 0.1521 g of crude oil which was a 4:6 mixture of starting material to product, respectively. This material was dissolved in NMP (3 mL), treated with D PEA (0.07 mL, 0.38 mmol) and isopropyl amine (0.2 mL) and heated in a sealed tube at 115 C overnight. After cooling, the reaction mixture was diluted with water and EtOAc. The aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed with H20, IN HC1 (2x), saturated NaHC03, H20 and brine before drying with Na2S04. The material was filtered and concentrated under reduced pressure to give 0.1656 g of crude oil Purification of this material was not required. This aniline (0.1544 g, 0.55 mmol), benzoylpiperazine hydrochloride (0.1496 g, 0.66 mmol) and NaOiBu (0.1586 g, 1.65 mmol) were added to a tube. The tube was evacuated and flushed with argon for three cycles. Toluene (1.7 mL) and NMP (1.0 mL) were then added and the mixture was degassed with argon for 30 minutes. Pd2(dba)3 (0.0101 g, 0.01 1 mmol) and BetaGamma AlphaRho (0.0137 g, 0.022 mmol) were then added, the tube was sealed and heated overnight at 80 C. After cooling, the mixture was diluted with water and EtOAc. The aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed with H20, IN HC1 (2x), saturated NaHC03, H20 and brine before drying with Na2S04. The material was filtered and concentrated under reduced pressure to give a crude oil. Purification of this material via flash chromatography (20 % EtOAc / hexane) gave 0.125 g (58 % yield) of TRV 1166 (4-(3- (isopropylamino)-4-(trifluoromethyl)phenyl)piperazin-l-yl)(phenyl)methanone[00149] NMR (700 MHz, CDC13) delta = 7.46-7.41 (m, 5H), 7.30 (d, J = 8.4 Hz, 1 H), 6.21 (dd, J = 8.4, 2.1 Hz, 1H), 6.16 (s, 1H), 4.12-4.1 1 (m, 1H), 3.93 (br s, 2H), 3.68-3.66 (m, 1H), 3.59 (br s, 2H), 3.33 (br s, 2H), 3.18 (br s, 2H), 1.24 (d, J = 6.2 Hz, 6H).

Reference： [1]Patent: WO2012/119035,2012,A1 .Location in patent: Page/Page column 50-51

14
[ 142808-15-9 ]
[ 1396778-56-5 ]

Reference： [1]Patent: WO2012/119035,2012,A1

15
[ 142808-15-9 ]
[ 1396778-68-9 ]

Reference： [1]Patent: WO2012/119035,2012,A1

16
[ 142808-15-9 ]
[ 288086-98-6 ]
[ 1395078-50-8 ]

Yield	Reaction Conditions	Operation in experiment
33.2%		step 2: To a solution of 4-bromo-2-fluoro-l-(trifluoromethyl)benzene (4.854 g, 19.98 mmol) and ether (50 mL) cooled to -78 C was added butyl lithium (7.990 mL, 19.98 mmol) slowly over 10 min. The reaction was transferred via cannula to a solution of 74 (4.30 g, 16.65 mmol) in THF (50 mL) cooled to -78 C. The reaction was stirred for 10 min after all aryl lithium was added. The reaction was quenched with water and extracted with DCM. The organic layer was concentrated and the crude product purified by Si02 chromatography eluting with an EtOAc/hexane (1 to 5% EtOAc). A close running impurity was not removed by this purification. A Si02 column was run eluting with an Et20/hexane gradient (1 to 3% Et20). The impurity was still present and the compound was finally purified on a SP4 reverse phase column chromatography eluting with MeCN/water gradient (65 to 100% MeCN) to afford 2.105 g (33.2%) of (R)-tert-butyl 2-(3-fluoro-4-(trifluoromethyl)benzoyl)-pyrrolidine-l-carboxylate (76).
33.2%		[00199] step 2: (R)-tert-butyl 2-(3 -fluoro-4-(trifluoromethyl)benzoyl)pyrrolidine- 1 -carboxylate. To a stirred solution of 4-bromo-2-fluoro-l-(trifluoromethyl)benzene (4.854 g, 19.98 mmol) and ether (50 mL) cooled to -78 C under nitrogen was added w-butyl lithium (7.99 mL, 19.98 mmol) slowly over 10 min. The reaction was transferred via cannula to a solution of 42b (4.30 g, 16.65 mmol) in THF (50 mL) cooled to -78 C. The reaction was stirred for 10 min after all aryl lithium was added. The reaction was quenched with water and extracted with DCM. The organic layer was dried (MgS04), concentrated and the crude product purified by Si02 chromatography eluting with an EtOAc/hexane gradient (1 to 5% EtOAc). A close running impurity was not removed by this purification. The compound was further purified on a SP4 reverse phase column chromatography eluting with MeCN/water gradient (65 to 100% MeCN) to afford 2.105 g (33.2%) of 44.

Reference： [1]Patent: WO2012/118850,2012,A1 .Location in patent: Page/Page column 138
[2]Patent: WO2013/20062,2013,A1 .Location in patent: Paragraph 00199

17
[ 142808-15-9 ]
2-fluoro-4-(4-propylcyclohexyl)-1-(1,2,2-trifluorovinyl)benzene [ No CAS ]
(E)-1-(1,2-difluoro-2-[3-fluoro-4-(trifluoromethyl)phenyl]vinyl)-2-fluoro-4-(4-propylcyclohexyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%		To a reaction vessel under a nitrogen atmosphere, <strong>[142808-15-9]4-bromo-2-fluoro-1-(trifluoromethyl)benzene</strong> (2.28 g) and diethyl ether (70 ml) were added, and cooling was carried out to-70C. Thereto, a n-butyllithium (1.57 M) n-hexane solution (7.10 ml) was added dropwise in a temperature range of -70C to -65C, and stirring was carried out for another 1 hour. Subsequently, a diethyl ether (10 ml) solution of compound (T-9) (2.68 g) was added dropwise in a temperature range of -70C to -65C, and stirring was carried out for 4 hours while returning to room temperature. The resultant reaction mixture was poured into ice water (100 ml), and mixing was carried out. Toluene (100 ml) was added to separate layers into an organic layer and an aqueous layer, and an extraction operation was performed. The resultant organic layer was sequentially washed with a 1 N hydrochloric acid solution, a saturated aqueous solution of sodium hydrogencarbonate and water, and drying over anhydrous magnesium sulfate was carried out. The resultant solution was concentrated under reduced pressure, and a residue was purified by fractionation by means of column chromatography (silica gel; heptane), and further purified by recrystallization from a heptane/Solmix A-11 mixed solvent, and thus (E)-1-(1,2-difluoro-2-[3-fluoro-4-(trifluoromethyl)phenyl]vinyl)-2 -fluoro-4-(4-propylcyclohexyl)benzene (1-1-25) (2.24 g) was obtained. The yield based on compound (T-9) was 57%. Chemical shifts according to 1H-NMR analysis were as described below, and the compound obtained could be identified to be (E)-1-(1,2-difluoro-2-[3-fluoro-4-(trifluoromethyl)phenyl]vinyl)-2 -fluoro-4-(4-propylcyclohexyl)benzene. Chemical shifts delta (ppm; CDCl3); 7.72 - 7.57 (m, 3H), 7.46 (dd, J = 7.65 Hz, J = 7.65 Hz, 1H), 7.10 (d, J = 8.05 Hz, 1H), 7.04 (d, J = 11.7 Hz, 1H), 2.52 (tt, J = 9.15 Hz, J = 3.15 Hz, 1H), 1.96 - 1.85 (m, 4H), 1.50 - 1.38 (m, 2H), 1.38 - 1.26 (m, 3H), 1.26 - 1.19 (m, 2H), 1.12 - 1. 01 (m, 2H), 0.91 (t, J = 7.30 Hz, 3H). A phase transition temperature of compound (1-1-25) obtained was as described below. Phase transition temperature: C 104 N 125 I.

Reference： [1]Patent: EP2522649,2012,A1 .Location in patent: Page/Page column 48-49

18
[ 142808-15-9 ]
[ 139345-12-3 ]
[ 1416557-50-0 ]

Yield	Reaction Conditions	Operation in experiment
17%		To a solution of <strong>[142808-15-9]4-bromo-2-fluorobenzotrifluoride</strong> (410.7 mg, 1 .69 mmol) in dry tetrahydrofuran (6 mL) under argon at 0 C was added isopropylmagnesium chloride (0.85 mL, 1 .69 mmol). After warming to room temperature the reaction was stirred for 40 minutes and then the reaction was cooled to -78 C. A solution of the product of Example 1 b (200 mg, 1 .30 mmol) in dry tetrahydrofuran (1 mL) was slowly added and the reaction was stirred for 2 hours. The mixture was quenched by the addition of saturated aqueous ammonium chloride (15 mL) and after warming to room temperature the reaction was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 90:1 -> 80:1 ) to give the title compound as a white solid (89 mg, Yield: 17%). Mp = 71 -73 C; Rf = 0.5 (10:1 ) petroleum ether/: ethyl acetate); 1H NMR (400 MHz, CDCI3) delta 7.55-7.51 (m, 1 H), 7.30-7.25 (m, 2 H), 5.09 (d, J = 5.6 Hz, 1 H), 1 .84-1 .79 (m, 2 H), 1 .65-1 .61 (m, 1 H), 1 .50-1 .46 (m, 3 H), 1 .39 (d, J = 1 1 .2 Hz, 1 H), 1 .31 -1 .25 (m, 1 H), 1 .15 (s, 3 H), 1 .07 (s, 3 H), 1 .0-0.90 (m, 1 H), 0.57 (d, J = 6.4 Hz, 3 H) ppm; [a]D22 7 = +13.6 (c = 0.22, dichloromethane).

Reference： [1]Patent: WO2012/174064,2012,A1 .Location in patent: Page/Page column 121-122

19
[ 142808-15-9 ]
[ 1416557-51-1 ]

Reference： [1]Patent: WO2012/174064,2012,A1

20
[ 142808-15-9 ]
[ 1416557-52-2 ]

Reference： [1]Patent: WO2012/174064,2012,A1

21
[ 142808-15-9 ]
[ 472-66-2 ]
[ 1441167-81-2 ]

Yield	Reaction Conditions	Operation in experiment
36%		Into a 50 mL dry, round bottom flask fitted with a magnetic stirring bar, a dropping funnel (25 mL) and a refluxing condenser was placed magnesium turnings (129 mg, 5.3 mmol) and anhydrous diethyl ether (4 mL). Anhydrous diethyl ether (16 mL) was added to the dropping funnel followed by 4-bromo- 2-fluoro-1-(trifluoromethyl)benzene (1.17 g, 4.8 mmol). A portion of the 4- bromo-2-fluoro-1-(trifluoromethyl)benzene solution (2 mL) as well as iodine (5 mg) was added to the flask which was then heated to reflux and stirred. Heating was stopped and the remainder of the 4-bromo-2-fluoro-1- (trifluoromethyl)benzene solution was added dropwise to the flask at such a rate that the solvent refluxed gently (about 10 minutes). After the addition was complete, the reaction was heated to reflux for 2 hours. The mixture was cooled to -78 C and a solution of 2-(2,6,6-trimethylcyclohex-1- enyl)acetaldehyde (200 mg, 1.2 mmol) in diethyl ether (3 mL) was added dropwise via syringe. The reaction was allowed to warm to room temperature and stirred for 4 hours. The reaction was quenched by addition of saturated aqueous ammonium chloride (10 mL). The mixture was diluted with water (20 mL) and the organics were extracted with diethyl ether (30 mL x 2). The combined organic phase was washed with brine (60 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleumether/ethyl acetate = 100/1 ) to afford the title compound as a yellow oil (138 mg, Yield: 35%). Rf = 0.6 (10:1 petroleum ether/ethyl acetate); 1H NMR (400 MHz, CDCI3) delta 7.57 (t, J = 7.6 Hz, 1 H), 7.30-7.23 (m, 2H), 4.89 (t, J = 7.4 Hz, 1 H), 2.48-2.46 (m, 2H), 2.22 (d, J = 1 .2 Hz, 1 H), 2.12-1.96 (m, 2H), 1.68 (s, 3H), 1 .68-1 .62 (m, 2H), 1 .51 -1 .48 (m, 2H), 1 .07 (s, 3H), 1.06 (s, 3H) ppm; Mass spectrum (ESI +ve) m/z 331 (M + H+).

Reference： [1]Patent: WO2013/81642,2013,A1 .Location in patent: Page/Page column 91-92

22
[ 142808-15-9 ]
[ 201230-82-2 ]
[ 1885-29-6 ]
[ 1570097-62-9 ]

Reference： [1]Green Chemistry,2014,vol. 16,p. 1336 - 1343

23
[ 253-69-0 ]
[ 142808-15-9 ]
[ 501-53-1 ]
[ 1589601-98-8 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2989 - 3004

24
[ 142808-15-9 ]
methyl 4-amino-3-chloro-6-(3-fluoro-2-methyl-4-(trifluoromethyl)phenyl)picolinate [ No CAS ]

Reference： [1]Patent: US2014/274703,2014,A1

25
[ 142808-15-9 ]
4-amino-3-chloro-6-(3-fluoro-2-methyl-4-(trifluoromethyl)phenyl)picolinic acid [ No CAS ]

Reference： [1]Patent: US2014/274703,2014,A1

26
[ 142808-15-9 ]
[ 74-88-4 ]
1-bromo-3-fluoro-2-methyl-4-(trifluoromethyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		Place <strong>[142808-15-9]4-bromo-2-fluorotrifluorotoluene</strong> (29.2 g, 120 mmol, 1 eq.) In a dropping funnel and set aside. Diisopropylamine (14.6g, 144mmol, 1.2eq.) And 220ml of tetrahydrofuran were added to the reaction flask, cooled to -78 C, and n-butyllithium (52.8ml, 132mmol, 1.1eq.) Was added dropwise under the protection of nitrogen. After the dropwise addition, the mixture was stirred at 25 C for 1 hour. Recool to -78 C and add <strong>[142808-15-9]4-bromo-2-fluorotrifluorotoluene</strong> dropwise. After the dropwise addition, the mixture was stirred at -78 C for 2 hours. Iodomethane (18.7g, 132mmol, 1.1eq.) Was added dropwise, and the temperature was gradually raised to 25 C for 16 hours.[0058]After the reaction was completed, it was cooled in an ice water bath, and 150 ml of saturated ammonium chloride solution was added dropwise for quenching. It was extracted with ethyl acetate, and the organic phase was concentrated to obtain 26.8 g of yellow oily 1-bromo-3-fluoro-2-methyl-4- (trifluoromethyl) benzene in 87% yield. Used directly in the next step.
80%		Example 28 Preparation of 1-bromo-3-fluoro-2-methyl-4-(trifluoromethyl)benzene To a stirred solution of bis(isopropyl)amine (1.383 mL, 9.87 mmol) in THF (27.4 mL) at -78 C. was added n-butyllithium (3.62 mL, 9.05 mmol). The resulting pale yellow solution was stirred at -78 C. for 15 min, warmed to 0 C. for 15 min, then recooled to -78 C. for 15 min. 4-Bromo-2-fluoro-1-(trifluoromethyl)benzene (2 g, 8.23 mmol) was then added, and the resulting solution was stirred at -78 C. for 2 h. Iodomethane (0.512 mL, 8.22 mumol) was then added. The solution was allowed to slowly warm to room temperature (rt) and stirred overnight. The reaction mixture was diluted with 0.1 M hydrochloric acid (HCl) and extracted with dichloromethane. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude brown residue was purified via flash chromatography on silica (5-30% ethyl acetate (EtOAc)/Hexanes) to yield the title compound as a clear oil (1.7 g, 80%): 1H NMR (400 MHz, CDCl3) delta 7.57-7.41 (m, 1H), 7.32-7.26 (m, 1H), 2.41 (dd, J=10.0, 8.3 Hz, 3H); 19F NMR (376 MHz, CDCl3) delta -61.2, -105.7, -108.1; IR (thin film) 2177, 1319 cm-1.

Reference： [1]Patent: CN110885290,2020,A .Location in patent: Paragraph 0019; 0029-0032; 0040-0043; 0051-0054
[2]Patent: US2014/274703,2014,A1 .Location in patent: Paragraph 0246; 0247

27
[ 142808-15-9 ]
[ 75-61-6 ]
4-(bromodifluoromethyl)-2-fluoro-1-(trifluoromethyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%		Under an argon atmosphere, 4-bromo-2-fluoro-1- (trifluoromethyl) benzene (155 mul, 1.0 mmol) and metallic magnesium (28.8 mg, 1.2 mmol) were added to THF (5.0 ml) At room temperature overnight to prepare a THF solution of 3-fluoro-4-trifluoromethylphenyl magnesium bromide. A THF solution of the prepared 3-fluoro-4-trifluoromethylphenylmagnesium bromide was added dropwise to a THF solution (2.0 M, 490 mul, 1.2 mmol) of dibromodifluoromethane cooled to -78 C., and the temperature was raised to room temperature And stirred for 8 hours. Saturated ammonium chloride aqueous solution (2.0 ml) was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with water and saturated sodium chlorideWashed with an aqueous solution of potassium, dried and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate-hexane) and recycle GPC (chloroform) to give 4- (bromodifluoromethyl) -2-fluoro-1- (trifluoromethyl) benzene 166.3 mg, 57%) as a yellow solid.
22%		General procedure: To a stirred solution of Ar-X 9 (1.0 mmol) in THF(4.5 ml) was added dropwise a solution of i-PrMgCl in Et2O (2.0 M, 0.53 ml, 1.06 mmol) at -40 C under Ar and the resulting mixture was stirred at -40 C for 3 h and cooled to -78 C. To a stirred solution of dibromodifluoromethane in THF (2.46 M, 0.49 ml, 1.2 mmol) was added dropwise the prepared solution of Ar-MgCl 10 in THF via cannula at -78 C and the resulting mixture was gradually warmed to room temperature over 8 h. The reaction was quenched with saturated aqueous NH4Cl (10 ml) and extracted with EtOAc (10 ml x 3). The combined extracts were dried over Na2SO4. Concentration of the solvent in vacuo afforded a residue, which was purified by silica gel column chromatography and recycle GPC to give Ar-CF2Br 11.

Reference： [1]Patent: JP2015/67547,2015,A .Location in patent: Paragraph 0028
[2]Tetrahedron Letters,2014,vol. 55,p. 6839 - 6843

28
[ 142808-15-9 ]
3-(2-aminobenzo[d]thiazol-4-yl)-N,N-bis(4-methoxybenzyl)-2-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide [ No CAS ]
3-(2-aminobenzo[d]thiazol-4-yl)-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide [ No CAS ]