[ CAS No. 160968-99-0 ] {[proInfo.proName]}

Name: 160968-99-0|2-(2,2,2-Trifluoroethoxy)phenol|97%
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Product Details of [ 160968-99-0 ]

CAS No. :	160968-99-0	MDL No. :	MFCD11181824
Formula :	C₈H₇F₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VDWGLBLCECKXRU-UHFFFAOYSA-N
M.W :	192.14	Pubchem ID :	13085347
Synonyms :

Calculated chemistry of [ 160968-99-0 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	3
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.96
TPSA :	29.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.75 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.79
Log Po/w (XLOGP3) :	2.43
Log Po/w (WLOGP) :	3.59
Log Po/w (MLOGP) :	1.95
Log Po/w (SILICOS-IT) :	2.23
Consensus Log Po/w :	2.4

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.71
Solubility :	0.378 mg/ml ; 0.00197 mol/l
Class :	Soluble
Log S (Ali) :	-2.69
Solubility :	0.391 mg/ml ; 0.00203 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.86
Solubility :	0.267 mg/ml ; 0.00139 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.3

Safety of [ 160968-99-0 ]

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

Application In Synthesis of [ 160968-99-0 ]

* 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 [ 160968-99-0 ]
Downstream synthetic route of [ 160968-99-0 ]

[ 160968-99-0 ] Synthesis Path-Upstream 1~7

1
[ 106854-74-4 ]
[ 160968-99-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With boron tribromide In dichloromethane for 2 h;	A 1 M solution of boron tribromide (30 mL, 0.03 mol) in CH2Cl2 was added to a solution ofintermediate 2 (4.3 g, 0.02 mol) in anhydrous CH2Cl2 (50 mL) at -20 °C. The reaction mixture waswarmed to room temperature and, after, quenched by addition of excess saturated aqueous sodiumbicarbonate solution (40 mL). The organic layer was dried over Na2SO4, filtered, and concentratedunder reduced pressure. The crude material was sufficiently pure to be used directly in the next step(yield 98percent). Yellow oil (3.8 g); UPLC/MS purity 99percent, tR = 5.37. C8H7F3O2, MW 192.14, MonoisotopicMass 192.04, [M + H]- 191.0. 1H-NMR (300 MHz, CDCl3) δ 4.36 (q, J = 8.4 Hz, 2H, O–CH2–CF3),6.81–7.11 (m, 4H, Ar–H), 9.72 (br.s., 1H, O–H). 13C-NMR (75 MHz, CDCl3) δ 56.2, 68.1, 119.2, 121.5,122.4, 123.7, 126.4, 127.3, 136.4

Reference： [1] Molecules, 2018, vol. 23, # 9,
[2] Patent: US5387603, 1995, A,
[3] Patent: WO2011/30356, 2011, A2, . Location in patent: Page/Page column 23
[4] Patent: WO2011/101864, 2011, A1, . Location in patent: Page/Page column 21-22
[5] Patent: US2012/165548, 2012, A1, . Location in patent: Page/Page column 11

2
[ 353-83-3 ]
[ 120-80-9 ]
[ 160968-99-0 ]

Reference： [1] Patent: WO2011/30356, 2011, A2, . Location in patent: Page/Page column 23
[2] Patent: US2012/165548, 2012, A1, . Location in patent: Page/Page column 11

3
[ 433-06-7 ]
[ 120-80-9 ]
[ 160968-99-0 ]

Reference： [1] Patent: WO2011/101864, 2011, A1, . Location in patent: Page/Page column 22

4
[ 90-05-1 ]
[ 160968-99-0 ]

Reference： [1] Patent: WO2011/30356, 2011, A2,
[2] Patent: US2012/165548, 2012, A1,
[3] Patent: WO2011/101864, 2011, A1,
[4] Molecules, 2018, vol. 23, # 9,

5
[ 75-89-8 ]
[ 65109-75-3 ]
[ 65109-81-1 ]
[ 129560-99-2 ]
[ 65109-80-0 ]
[ 160968-99-0 ]

Reference： [1] Journal of the American Chemical Society, 1982, vol. 104, # 23, p. 6393 - 6397

6
[ 105-36-2 ]
[ 160968-99-0 ]
[ 160969-01-7 ]
[ 160969-03-9 ]

Reference： [1] Patent: US5387603, 1995, A,

7
[ 160968-99-0 ]
[ 160969-03-9 ]

Reference： [1] Patent: WO2011/101864, 2011, A1,

[ 160968-99-0 ] Synthesis Path-Downstream 1~35

1
[ 75-89-8 ]
[ 65109-75-3 ]
[ 65109-81-1 ]
[ 129560-99-2 ]
[ 65109-80-0 ]
[ 160968-99-0 ]

Reference： [1]Journal of the American Chemical Society,1982,vol. 104,p. 6393 - 6397

2
[ 105-36-2 ]
[ 160968-99-0 ]
[ 160969-01-7 ]
[ 160969-03-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In ethyl acetate; N,N-dimethyl-formamide;	Reference Example 6 2-[2-(2,2,2-Trifluoroethoxy)phenoxy]ethyl methanesulfonate To a solution of <strong>[160968-99-0]2-(2,2,2-trifluoroethoxy)phenol</strong> (200 mg) in dry N,N-dimethylformamide (2 ml) were added ethyl bromoacetate (138 mul) and potassium carbonate (216 mg), and the mixture was reacted with stirring at room temperature for 1 hour, and then for 1 hour at 60 C. To the reaction mixture was added ethyl acetate, and ethyl acetate solution was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 270 mg of ethyl 2-(2,2,2-trifluoroethoxy)phenoxyacetate as an oil. IR (neat): upsilonC=O 1760 cm-1

Reference： [1]Patent: US5387603,1995,A

3
[ 160968-99-0 ]
[ 106-93-4 ]
[ 160969-00-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate; potassium iodide; In acetone; at 60℃; for 48.0h;	Phenol 3 (4.8 g, 0.025 mol) was dissolved in acetone (30 mL). Then K2CO3 (10.4 g, 0.075 mol)and catalytic amount of KI (0.08 g, 0.0005 mol) were added, followed by dropwise addition of1,2-dibromoethane (12.9 mL, 0.15 mol). The reaction was refluxed for 48 h. Inorganic residues werefiltered off and organic mixture was concentrated under reduced pressure. The obtained crude productwas purified using silica gel with AcOEt/Hexane (0.5/9, v/v) as an eluting system (isolated yield75%). Yellow oil (5.61 g); UPLC/MS purity 97%, tR = 7.41. C10H10BrF3O2, MW 299.09, MonoisotopicMass 297.98, [M + H]+ 300.2. 1H-NMR (300 MHz, CDCl3) delta 3.45 (t, J = 6.5 Hz, 2H, N-CH2-CH2), 4.29(t, J = 6.5 Hz, 2H, O-CH2-CH2), 4.36 (q, J = 8.4 Hz, 2H, O-CH2-CF3), 6.82 (dd, J = 5.2, 1.0 Hz, 1H,Ar-H), 6.99 (td, J = 7.6, 1.1 Hz, 1H, Ar-H), 7.14 (td, J = 8.0, 1.8 Hz, 1H, Ar-H), 7.24-7.28 (m, 1H, Ar-H).13C-NMR (75 MHz, CDCl3) delta 56.2, 64.1, 65.8, 68.1, 119.3, 121.5, 122.4, 123.7, 126.4, 127.3, 136.4.
	With hydrogenchloride; sodium hydroxide;	NMR (CDCl3) delta: 4.42(2H, q, J=7.9Hz), 5.53(1H, s), 6.80-7.10(4H, m) To an aqueous solution (15 ml) of sodium hydroxide (0.63 g) were added <strong>[160968-99-0]2-(2,2,2-trifluoroethoxy)phenol</strong> (2.85 g) and 1,2-dibromoethane (1.68 ml), and the mixture was reacted with stirring at 120 C. for 8 hours. To the reaction mixture was added concentrated hydrochloric acid (1.3 ml), and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (5/1) as eluent to give 1.78 g of 1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene as an oil NMR (CDCl3) delta: 3.67(2H, t, J=6.0Hz), 4.34(2H, t, J=6.0Hz), 4.43(2H, q, J=8.2Hz), 6.90-7.20(4H, m)

Reference： [1]Molecules,2018,vol. 23
[2]Patent: US5387603,1995,A

4
[ 106854-74-4 ]
[ 160968-99-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With boron tribromide; In dichloromethane; for 2.0h;	A 1 M solution of boron tribromide (30 mL, 0.03 mol) in CH2Cl2 was added to a solution ofintermediate 2 (4.3 g, 0.02 mol) in anhydrous CH2Cl2 (50 mL) at -20 C. The reaction mixture waswarmed to room temperature and, after, quenched by addition of excess saturated aqueous sodiumbicarbonate solution (40 mL). The organic layer was dried over Na2SO4, filtered, and concentratedunder reduced pressure. The crude material was sufficiently pure to be used directly in the next step(yield 98%). Yellow oil (3.8 g); UPLC/MS purity 99%, tR = 5.37. C8H7F3O2, MW 192.14, MonoisotopicMass 192.04, [M + H]- 191.0. 1H-NMR (300 MHz, CDCl3) delta 4.36 (q, J = 8.4 Hz, 2H, O-CH2-CF3),6.81-7.11 (m, 4H, Ar-H), 9.72 (br.s., 1H, O-H). 13C-NMR (75 MHz, CDCl3) delta 56.2, 68.1, 119.2, 121.5,122.4, 123.7, 126.4, 127.3, 136.4
	With boron tribromide; In dichloromethane;	To a solution of 1-methoxy-2-(2,2,2-trifluoroethoxy)benzene (3.83 g) in dry methylene chloride (50 ml) was added boron tribromide (3.1 ml) with stirring under ice cooling, and the mixture was reacted for 30 minutes. The reaction mixture was poured into an aqueous sodium bicarbonate solution (500 ml), and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (20/1) as eluent to give 2.37 g of 2-(2,2,2-trifluoroethoxy)phenol melting at 49-50 C. IR (KBr): upsilonOH 3310 cm-1
		Example-6 Preparation of 2-(2,2,2-trifluoroethoxy) phenol (XI) Boron tribromide (2.8 ml, 0.03 mole) was added to a solution of 1-methoxy-2-(2,2,2- trifluoroethoxy)benzene (X) (6.0 g, 0.03 mole) in methylene chloride (90 ml) with stirring below -10C. Reaction was stirred at -10 to -20C for 30 minutes. The reaction mixture was quenched using aqueous sodium bicarbonate solution. Organic layer was separated, washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure to give 4.0 g of (XI) as oil. Purity (by GC) = 95 %.

	With aluminum (III) chloride; ethanethiol; In dichloromethane; at 0 - 20℃; for 4.0h;	Example 2: Preparation of 2-(2,2,2-Trifluoroethoxy)phenol (VI):a) Route-1 : To a mixture of ethanethiol (2 ml) in methylene chloride (4 ml) was added aluminum chloride (6.77 g, 50.9 mmol) slowly at 0 C. The resulting solution was stirred for 10 min and 1-methoxy-2-(2,2,2-trifluoroethoxy) benzene (IV) (3.5 g, 16.9 mmol) in methylene chloride (4 ml) was added at 0C. The mixture was warmed to room temperature and stirred for 4 h. The mixture was diluted with water (50 ml), extracted with methylene chloride (3 X 100 ml) and concentrated under reduced pressure. The product was purified by column chromatography to give 3 g of 2-(2,2,2-trifluoroethoxy) phenol (VI) as a thick gel.
		Boron tribromide (2.8 ml, 0.03 mole) was added to a solution of 1-methoxy-2-(2,2,2-trifluoroethoxy)benzene (X) (6.0 g, 0.03 mole) in methylene chloride (90 ml) with stirring below -10 C. Reaction was stirred at -10 to -20 C. for 30 minutes. The reaction mixture was quenched using aqueous sodium bicarbonate solution. Organic layer was separated, washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure to give 4.0 g of (XI) as oil. Purity (by GC)=95%

Reference： [1]Molecules,2018,vol. 23
[2]Patent: US5387603,1995,A
[3]Patent: WO2011/30356,2011,A2 .Location in patent: Page/Page column 23
[4]Patent: WO2011/101864,2011,A1 .Location in patent: Page/Page column 21-22
[5]Patent: US2012/165548,2012,A1 .Location in patent: Page/Page column 11

5
[ 90-05-1 ]
[ 160968-99-0 ]

Reference： [1]Patent: WO2011/30356,2011,A2
[2]Patent: WO2011/101864,2011,A1
[3]Molecules,2018,vol. 23

6
[ 160968-99-0 ]
[ 107-07-3 ]
[ 160969-02-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 100 - 105℃; for 10.0h;	Example - 10 Preparation of 2-[2-(2,2,2-Trifluoro-ethoxy)-phenoxy]-ethanol (XIV) To a mixture of <strong>[160968-99-0]2-(2,2,2-trifluoroethoxy) phenol</strong> (XI) (6 g, 0.03 mole), N,N- dimethylformamide (50 ml) and potassium carbonate (13.0g, 0.09 mole) was added 2-chloroethanol (4.2 ml, 0.06 mole). Reaction mixture was heated to 100-105C and stirred for 10 hours. Reaction mass was filtered and the filtrate was concentrated under reduced pressure to distill out the N, N-Dimethyl formamide. To the residue was added water and product was extracted in ethyl acetate (50 ml). The organic layer was washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane (5/95) as eluent to give 4.0 g of (XIV) as oil. Purity (By GC) = 95 %
	With potassium carbonate; In N,N-dimethyl-formamide; at 100 - 105℃; for 10.0h;	To a mixture of <strong>[160968-99-0]2-(2,2,2-trifluoroethoxy)phenol</strong> (XI) (6 g, 0.03 mole), N,N-dimethylformamide (50 ml) and potassium carbonate (13.0 g, 0.09 mole) was added 2-chloroethanol (4.2 ml, 0.06 mole). Reaction mixture was heated to 100-105 C. and stirred for 10 hours. Reaction mass was filtered and the filtrate was concentrated under reduced pressure to distill out the N,N-Dimethyl formamide. To the residue was added water and product was extracted in ethyl acetate (50 ml). The organic layer was washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane (5/95) as eluent to give 4.0 g of (XIV) as oil. Purity (By GC)=95%

Reference： [1]Patent: WO2011/30356,2011,A2 .Location in patent: Page/Page column 25
[2]Patent: US2012/165548,2012,A1 .Location in patent: Page/Page column 11-12

7
[ 353-83-3 ]
[ 120-80-9 ]
[ 160968-99-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In dimethyl sulfoxide; at 120℃; for 6.0h;	Example-7 Preparation of 2-(2,2,2-trifluoroethoxy) phenol (XI) To a solution of catechol (5 g, 0.045 moles) in dimethylsulfoxide (25 ml) were added, potassium carbonate ( 12.55 g, 0.09 mole) and 2,2,2-trifluoroethyl iodide (4.77 g, 0.023 mole) under stirring. The reaction mixture was stirred vigorously at 120C for 6 hours. Water (150 ml) was added to the reaction mixture and the mixture was extracted in Toluene (250 ml).Organic layer was washed with 1 N Sodium hydroxide solution (150 ml), followed by brine wash. The extract was dried over sodium sulphate. The solvent was evaporated under reduced pressure to give 4.0 g of (XI) as oil. Purity (by GC) = 96 %
	With potassium carbonate; In dimethyl sulfoxide; at 120℃; for 6.0h;	To a solution of catechol (5 g, 0.045 moles) in dimethylsulfoxide (25 ml) were added, potassium carbonate (12.55 g, 0.09 mole) and 2,2,2-trifluoroethyl iodide (4.77 g, 0.023 mole) under stirring. The reaction mixture was stirred vigorously at 120 C. for 6 hours. Water (150 ml) was added to the reaction mixture and the mixture was extracted in Toluene (250 ml). Organic layer was washed with 1 N Sodium hydroxide solution (150 ml), followed by brine wash. The extract was dried over sodium sulphate. The solvent was evaporated under reduced pressure to give 4.0 g of (XI) as oil. Purity (by GC)=96%

Reference： [1]Patent: WO2011/30356,2011,A2 .Location in patent: Page/Page column 23
[2]Patent: US2012/165548,2012,A1 .Location in patent: Page/Page column 11

8
[ 4360-63-8 ]
[ 160968-99-0 ]
[ 1269801-74-2 ]

Yield	Reaction Conditions	Operation in experiment
		ExampIe-8 Preparation of 2-[2-(2,2,2-trifluoro ethoxy) phenoxy ethyl]-[1,3] dioxalane (XII) Mixture of <strong>[160968-99-0]2-(2,2,2-trifluoroethoxy)phenol</strong> (XI) (6 g, 0.031 mole), N-methyl-2- pyrrolidone (30 ml), potassium carbonate ( 8.6 g 0.062 mole) and Bromo acetaldehyde ethylene glycol ( 6.26 g, 0.037 mole) was heated to 115-120C and stirred for 5 hours. Water (120 ml) was added to reaction mixture at ambient temperature and pH adjusted to 3-4 with mineral acid. The mixture was extracted using Ethyl acetate (200 ml). Organic layer was washed with aqueous sodium bicarbonate solution followed by water. Organic layer was dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane (5/95) as eluent to give 4.0 g of (XII) as colourless solid, melting at 37.6-39.6C.Purity (By GC) = 98 %IR (KBr): 1748.8, 1598.6, 1509, 1451.5, 1261.1, 1163, 1127.2, 1055.9, 1047.1 cm'1 1H NMR (300 MHz, CDC13): 3.93-3.98 (2H, d), 4.05-4.08 (4H,m), 4.36-4.45(2H,q), 5.314-5.338 (lH, t) , 6.90-7.05 (4H, m), ppmI3C NMR (75MHz, CDC13): 65.36(2C), 67.39-68.79(lC), 70.01(1C), 101.89(1C), 114.8, 118.10, 121.87, 124.18 (4C), 149.62 (1C), 147.48(1C), 128.22-129.03(1 C)
	With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 115 - 120℃; for 5.0h;	Mixture of <strong>[160968-99-0]2-(2,2,2-trifluoroethoxy)phenol</strong> (XI) (6 g, 0.031 mole), N-methyl-2-pyrrolidone (30 ml), potassium carbonate (8.6 g 0.062 mole) and Bromo acetaldehyde ethylene glycol (6.26 g, 0.037 mole) was heated to 115-120 C. and stirred for 5 hours. Water (120 ml) was added to reaction mixture at ambient temperature and pH adjusted to 3-4 with mineral acid. The mixture was extracted using Ethyl acetate (200 ml). Organic layer was washed with aqueous sodium bicarbonate solution followed by water. Organic layer was dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane (5/95) as eluent to give 4.0 g of (XII) as colourless solid, melting at 37.6-39.6 C.Purity (By GC)=98%IR (Mk): 1748.8, 1598.6, 1509, 1451.5, 1261.1, 1163, 1127.2, 1055.9, 1047.1 cm-1 1H NMR (300 MHz, CDCl3): 3.93-3.98 (2H, d), 4.05-4.08 (4H, m), 4.36-4.45 (2H, q), 5.314-5.338 (1H, t), 6.90-7.05 (4H, m), ppm13C NMR (75 MHz, CDCl3): 65.36 (2C), 67.39-68.79 (1C), 70.01 (1C), 101.89 (1C), 114.8, 118.10, 121.87, 124.18 (4C), 149.62 (1C), 147.48 (1C), 128.22-129.03 (1C)

Reference： [1]Patent: WO2011/30356,2011,A2 .Location in patent: Page/Page column 23; 24
[2]Patent: US2012/165548,2012,A1 .Location in patent: Page/Page column 11

9
[ 160968-99-0 ]
[ 160970-54-7 ]

Reference： [1]Patent: WO2011/30356,2011,A2
[2]Patent: WO2011/30356,2011,A2
[3]Patent: WO2011/30356,2011,A2
[4]Patent: WO2011/30356,2011,A2
[5]Patent: US2012/165548,2012,A1
[6]Patent: US2012/165548,2012,A1
[7]Patent: US2012/165548,2012,A1
[8]Patent: US2012/165548,2012,A1

10
[ 160968-99-0 ]
[ 885340-11-4 ]

Reference： [1]Patent: WO2011/30356,2011,A2
[2]Patent: WO2011/30356,2011,A2
[3]Patent: US2012/165548,2012,A1
[4]Patent: US2012/165548,2012,A1

11
[ 160968-99-0 ]
[ 885340-13-6 ]

Reference： [1]Patent: WO2011/30356,2011,A2
[2]Patent: WO2011/30356,2011,A2
[3]Patent: US2012/165548,2012,A1
[4]Patent: US2012/165548,2012,A1

12
[ 160968-99-0 ]
[ 1269801-73-1 ]

Reference： [1]Patent: WO2011/30356,2011,A2
[2]Patent: WO2011/30356,2011,A2
[3]Patent: US2012/165548,2012,A1
[4]Patent: US2012/165548,2012,A1

13
[ 160968-99-0 ]
[ 540-51-2 ]
[ 160969-02-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 90 - 100℃; for 66.0h;	Example 4: Preparation of 2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethanol (I):a) Route-1 : To a solution of <strong>[160968-99-0]2-(2,2,2-trifluoroethoxy) phenol</strong> (VI) (37 g, 192.7 mmol) in acetonitrile (370 ml) was added K2CO3 (79.7 g, 578.1 mmol) and followed by addition of 2-bromoethanol (VII) (48.17 g, 385.1 mmol) at room temperature. The mixture was stirred for 66 hrs at 90-100C. The reaction mixture was filtered and the solvent was evaporated under vacuum. The crude was diluted with ethyl acetate (400 ml) and washed with water (200 ml). The solvent was evaporated under vacuum to give 35 g of 2-[2-(2,2,2- trifluoroethoxy)phenoxy]ethanol (I) as an oil. (HPLC purity is 85-90%).

Reference： [1]Patent: WO2011/101864,2011,A1 .Location in patent: Page/Page column 22-23

14
[ 433-06-7 ]
[ 120-80-9 ]
[ 160968-99-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 24.0h;Sealed vessel;	b) Route-2: To a solution of Pyrocatechol (50 g, 454.5 mmol) in DMF (400 ml) was added K2C03 (188.1 g, 1363 mmol) and 2,2,2-trifluoroethyl p- toluenesulfonate (III) (115.4 g, 454.5 mmol) at room temperature. The mixture was stirred at 1 0C in a sealed vessel for 24 hrs. The mixture was diluted with water (750 ml) and extracted with ethyl acetate (250 ml). The ethyl acetate layer was washed with water (500 ml) and the solvent was evaporated under vacuum. The obtained crude material was purified by column chromatography to give 37 g of 2-(2,2,2-trifluoroethoxy)phenol (VI) as a thick gel.

Reference： [1]Patent: WO2011/101864,2011,A1 .Location in patent: Page/Page column 22

15
[ 160968-99-0 ]
[ 160969-03-9 ]

Reference： [1]Patent: WO2011/101864,2011,A1

16
[ 160968-99-0 ]
C₃₂H₃₀⁽²⁾H₄F₃N₃O₄ [ No CAS ]

Reference： [1]Heterocyclic Communications,2017,vol. 23,p. 187 - 195

17
[ 160968-99-0 ]
C₂₅H₂₈⁽²⁾H₄F₃N₃O₄ [ No CAS ]

Reference： [1]Heterocyclic Communications,2017,vol. 23,p. 187 - 195

18
[ 160968-99-0 ]
C₄₀H₃₈⁽²⁾H₄F₃N₃O₆ [ No CAS ]

Reference： [1]Heterocyclic Communications,2017,vol. 23,p. 187 - 195

19
[ 22581-63-1 ]
[ 160968-99-0 ]
C₁₀H₆⁽²⁾H₄BrF₃O₂ [ No CAS ]

Reference： [1]Heterocyclic Communications,2017,vol. 23,p. 187 - 195

20
[ 160968-99-0 ]
4-fluoro-N-[(1-{2-[(2,2,2-trifluoroethoxy)phenoxy]ethyl}piperidin-4-yl)methyl]benzenesulfonamide [ No CAS ]