[ CAS No. 261762-56-5 ] {[proInfo.proName]}

Name: 261762-56-5|1-Chloro-2-fluoro-3-methoxybenzene|95%
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SKU: A216563
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Quality Control of [ 261762-56-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 261762-56-5 ]

Product Details of [ 261762-56-5 ]

CAS No. :	261762-56-5	MDL No. :	MFCD01631570
Formula :	C₇H₆ClFO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CVFVXCYDOOGQCJ-UHFFFAOYSA-N
M.W :	160.57	Pubchem ID :	2773584
Synonyms :

Calculated chemistry of [ 261762-56-5 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	37.9
TPSA :	9.23 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) :	-5.36 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.12
Log Po/w (XLOGP3) :	2.71
Log Po/w (WLOGP) :	2.91
Log Po/w (MLOGP) :	2.84
Log Po/w (SILICOS-IT) :	2.88
Consensus Log Po/w :	2.69

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.92
Solubility :	0.193 mg/ml ; 0.0012 mol/l
Class :	Soluble
Log S (Ali) :	-2.56
Solubility :	0.445 mg/ml ; 0.00277 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.41
Solubility :	0.0626 mg/ml ; 0.00039 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.51

Safety of [ 261762-56-5 ]

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 [ 261762-56-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 261762-56-5 ]

[ 261762-56-5 ] Synthesis Path-Downstream 1~37

1
[ 261762-56-5 ]
[ 68-12-2 ]
[ 1002344-90-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example 3 5-[1-(2-Chloro-3-fluoro-4-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-([methylsulfanyl]methyl)propyl]amino}-1H-quinolin-2-one2-Chloro-3-fluoro-4-methoxybenzaldehyde; 1 g (6.2 mmol) <strong>[261762-56-5]3-Chloro-2-fluoroanisole</strong> in 20 ml THF are cooled to -70 C. and 2.7 ml of a 2.5 M n-butyl lithium solution in hexane are added. After one hour at -70 3.93 ml DMF in 7 ml THF are added at -70 C. and the mixture is stirred another hour at -70 C. 15 ml of a 1 M aqueous HCl are added and the reaction is warmed to ambient temperature over 18 hours. The reaction mixture is partitioned between diethyl ether and water. The aqueous phase is extracted with diethyl ether, the combined organic phases are washed with brine, dried over sodium sulfate and evaporated. The crude product is purified by chromatography on silica gel to yield 0.25 g 2-chloro-3-fluoro-4-methoxybenzaldehyde. 1H-NMR (CDCl3); delta=3.98 (s, 3H), 6.98 (dd, 1H), 7.75 (dd, 1H), 10.30 (s, 1H).
		1 g (6.2 mmol) <strong>[261762-56-5]3-Chloro-2-fluoroanisole</strong> in 20 ml THF was cooled to -70 C. and 2.7 ml of a 2.5 M n-butyl lithium solution in hexane were added. After one hour at -70 3.93 ml DMF in 7 ml THF were added at -70 C. and the mixture is stirred another hour at -70 C. 15 ml of a 1 M aqueous hydrochloric acid were added and the reaction was warmed to ambient temperature over 18 hours. The reaction mixture was partitioned between diethyl ether and water. The aqueous phase was extracted with diethyl ether, the combined organic phases were washed with brine, dried over sodium sulfate and evaporated. The crude product was purified by chromatography on silica gel to yield 0.25 g 2-chloro-3-fluoro-4-methoxybenzaldehyde. 1H-NMR (CDCl3); delta=3.98 (s, 3H), 6.98 (dd, 1H), 7.75 (dd, 1H), 10.30 (s, 1H).
		2-Chloro-3-fluoro-4-methoxybenzaldehyde 1g (6.2 mmol) <strong>[261762-56-5]3-Chloro-2-fluoroanisole</strong> in 20 ml THF was cooled to -70C and 2.7 ml of a 2.5 M n-butyl lithium solution in hexane were added. After one hour at -70 3.93 ml DMF in 7 ml THF were added at -70C and the mixture is stirred another hour at -70C. 15 ml of a 1 M aqueous hydrochloric acid were added and the reaction was warmed to ambient temperature over 18 hours. The reaction mixture was partitioned between diethyl ether and water. The aqueous phase was extracted with diethyl ether, the combined organic phases were washed with brine, dried over sodium sulfate and evaporated. The crude product was purified by chromatography on silica gel to yield 0.25 g 2-chloro-3-fluoro-4-methoxybenzaldehyde. 1H-NMR (CDCl3); delta = 3.98 (s, 3H), 6.98 (dd, 1H), 7.75 (dd, 1H), 10.30 (s, 1H).

Reference： [1]Patent: US2009/137564,2009,A1 .Location in patent: Page/Page column 13
[2]Patent: US2010/16338,2010,A1 .Location in patent: Page/Page column 12
[3]Patent: EP2149558,2010,A1 .Location in patent: Page/Page column 20
[4]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5741 - 5748

2
[ 261762-56-5 ]
[ 123707-26-6 ]
[ 1158734-20-3 ]

Yield	Reaction Conditions	Operation in experiment
		Example 12 5-[1-(4-Chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-(methoxymethyl)propyl]amino}-7-fluoro-1H-quinolin-2-one; (4-chloro-3-fluoro-2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methanone1 g (6.2 mmol) <strong>[261762-56-5]3-Chloro-2-fluoroanisole</strong> in 10 ml THF are cooled to -70 C. and 2.7 ml of a 2.5 M n-butyl lithium solution in hexane are added. After 1.5 hours at -70 1 g (6.9 mmol) N,N'-dimethoxy-N,N'-dimethyl urea in 6 ml THF are added at -70 C. and the mixture is stirred another hour at -70 C. 7.5 ml of a 2 M aqueous HCl are added and the reaction is warmed to ambient temperature over 18 hours. The reaction mixture is partitioned between diethyl ether and water. The aqueous phase is extracted with diethyl ether, the combined organic phases are washed with brine, dried over sodium sulfate and evaporated. The crude product is purified by chromatography on silica gel (ethyl acetate in hexane 0 to 30%) to yield 0.59 g 4-chloro-3-fluoro-2,N-dimethoxy-N-methylbenzamid. 1H-NMR (CDCl3); delta=3.35 (br, 3H), 3.49 (br, 3H), 3.98 (s, 3H), 6.99 (dd, 1H), 7.13 (dd, 1H).0.44 ml (5.1 mmol) 1,1,1-trifluoro-2,3-epoxypropane in 7.5 ml THF and 2.2 ml hexane are cooled to -100 C. and 2.03 ml of a 2.5 M n-butyl lithium solution (5.1 mmol) in hexane are added over 15 minutes while the temperature does not exceed -95 C. 10 minutes after complete addition 0.57 g (2.3 mmol) 4-chloro-3-fluoro-2,N-dimethoxy-N-methylbenzamid in 10 ml THF are added over 15 minutes while the temperature does not exceed -95 C. After 3 hours at -100 C. 2.3 ml diethyl ether is added and the reaction mixture is warmed to room temperature over 14 hours. The reaction is quenched by addition of saturated ammonium chloride solution. The phases were separated and the aqueous layer is extracted twice with diethyl ether, the combined organic phases washed with brine, dried over sodium sulphate and then evaporated to yield 570 mg of (4-chloro-3-fluoro-2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methanone. 1H-NMR (CDCl3); delta=2.99 (dq, 1H), 3.37 (d, 1H), 4.14 (d, 3H), 7.18 (m, 1H), 7.19 (m, 1H). 285 mg (0.95 mmol) (4-Chloro-3-fluoro-2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methanone are stirred with 622 mg (1.9 mmol) caesium carbonate in 6.7 ml methanol. The reaction is quenched by addition of water after one day. The aqueous layer is extracted with ethyl acetate, the combined organic phases are washed with brine, dried over sodium sulphate and then evaporated to yield 262 mg 1-(4-chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-methoxymethypropan-1-one. To 27 mg (0.15 mmol) 5-Amino-7-fluoro-1H-quinolin-2-one and 50 mg (0.15 mmol) 1-(4-chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-methoxymethypropan-1-one in 0.45 ml toluene and 0.13 ml 1,4-dioxane are added 33 mul acetic acid and 0.12 ml tetra butyl orthotitanate. The mixture is heated over 20 hours to 110 C., cooled to room temperature and poured into aqueous ammonium fluoride solution. Ethyl acetate is added and the mixture is stirred vigorously for 30 minutes. Phases are separated and two times extracted with ethyl acetate. The combined organic phases are concentrated to yield quantitatively 5-[1-(4-chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-methoxymethylpropylidene]amino}-7-fluoro-1H-quinolin-2-one. The raw imine in 4.2 ml methanol is cooled to 5 C. and 120 mg sodium boron hydride are added in multiple portions over the period of 72 hours. The reaction is quenched by addition of saturated ammonium chloride solution and diluted with water and ethyl acetate. The phases are separated, the aqueous layer is extracted with ethyl acetate, the combined organic phases are washed with brine and dried over sodium sulphate. After removal of the solvent preparative thin layer chromatography on silica gel (acetone in methylene chloride, 30%) yields 9.5 mg of the title compound.1H-NMR (CD3OD); delta=3.44 (s, 3H), 3.65 (m, 1H), 3.69 (d, 1H), 4.05 (d, 3H), 5.44 (s, 1H), 6.03 (dd, 1H), 6.30 (dd, 1H), 6.45 (d, 1H), 7.12 (dd, 1H), 7.35 (dd, 1H), 7.94 (d, 1H).

Reference： [1]Patent: US2009/137564,2009,A1 .Location in patent: Page/Page column 17-18

3
[ 261762-56-5 ]
[ 61676-62-8 ]
2-(4-chloro-3-fluoro-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
2-(2-chloro-3-fluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 40 Preparation of 2-(4-chloro-3-fluoro-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dloxaborolane [0281] [0282] To a 100 mL flask charged with THF (25 mL) was added <strong>[261762-56-5]1-chloro-2-fluoro-3-methoxybenzene</strong> (1 g, 6.23 mmol). The reaction flask was cooled to -78 C. in a dry ice acetone bath and n-butyllithium (0.399 g, 6.23 mmol) was added. After 40 min of stirring at -78 C. the reaction mixture was warmed to an internal temperature of -40 C. and the cooled to -78 C. in a dry ice acetone bath. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.159 g, 6.23 mmol) in THF (5 mL) was added in one portion. The dry ice/acetone bath was removed and the reaction mixture was allowed to warm to room temperature. The reaction mixture was nuetralized with 1N HCl solution and diluted with Et2O (50 mL) and water. The resulting organic layer was dried over Na2SO4, filtered and concentrated to give 1:1 mixture of 2-(4-chloro-3-fluoro-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 2-(2-chloro-3-fluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as light yellow oil that was used in the next step without further purification (300 mg): ESIMS m/z 271 ([M+H]+1).

Reference： [1]Patent: US2014/274703,2014,A1 .Location in patent: Paragraph 0281; 0282

4
[ 261762-56-5 ]
methyl 4-amino-3-chloro-6-(4-chloro-3-fluoro-2-methoxyphenyl)-5-fluoropicolinate [ No CAS ]

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

5
[ 261762-56-5 ]
C₂₃H₂₃ClF₄N₂O₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5741 - 5748

6
[ 261762-56-5 ]
C₁₈H₁₄ClFN₂O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5741 - 5748

7
[ 261762-56-5 ]
C₂₁H₁₆ClF₄NO₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5741 - 5748

8
[ 261762-56-5 ]
[ 4885-02-3 ]
[ 1002344-90-2 ]

Yield	Reaction Conditions	Operation in experiment
	With titanium tetrachloride; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere;	To a mixture of l-chloro-2-fluoro-3-methoxy-benzene (5.00 g, 31.1 mmol) in dichloromethane (40 mL) was added titanium tetrachloride (10.0 g, 52.9 mmol) dropwise at 0 C under a nitrogen. Dichloro(methoxy)methane (3.58 g, 31.1 mmol) was then added to the solution. Then the mixture was stirred at rt for 3 hours. On completion, the residue was poured into ice- water (50 mL) and extracted with ethyl acetate (50 mL). The combined organic layer was washed with brine (50 mL), dried with anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluted with (petroleum ether/ethyl acetate = 20/1 to 3/1) to give the title compound. LH NMR (400 MHz, DMSO-i) delta = 10.15 (s, 1H), 7.74 (d, J= 6.8 Hz, 1H), 7.37 (d, J= 5.9 Hz, 1H), 3.98 (s, 3H).
	With titanium tetrachloride; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere;	To a mixture of <strong>[261762-56-5]1-chloro-2-fluoro-3-methoxy-benzene</strong> (5.00 g, 31.1 mmol) in dichloromethane (40 mL) was added titanium tetrachloride (10.0 g, 52.9 mmol) dropwise at 0 C under nitrogen. Dichloro(methoxy)methane (3.58 g, 31.1 mmol) was then added to the solution. Then the mixture was stirred at rt for 3 hours. On completion, the residue was poured into ice- water (50 mL) and extracted with ethyl acetate (50 mL). The combined organic layer was washed with brine (50 mL), dried with anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluted with petroleum ether/ethyl acetate (20/1 to 3/1) to give the title compound. ?HNMR (400 IVIFIz, DMSO-d6) = 10.15 (s, 1H), 7.74 (d, J6.8 Hz, 1H), 7.37 (d, J 6.0 Hz, 1H), 3.98 (s, 3H).

Reference： [1]Patent: WO2017/156165,2017,A1 .Location in patent: Paragraph 00401-00403
[2]Patent: WO2017/156179,2017,A1 .Location in patent: Paragraph 00301; 00302; 00303

9
[ 261762-56-5 ]
(Z)-methyl-2-azido-3-(2-chloro-3-fluoro-4-methoxyphenyl)prop-2-enoate [ No CAS ]

Reference： [1]Patent: WO2017/156165,2017,A1

10
[ 261762-56-5 ]
methyl 4-chloro-5-fluoro-6-methoxy-1H-indole-2-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/156165,2017,A1

11
[ 261762-56-5 ]
methyl 4-chloro-5-fluoro-6-methoxy-1-methyl-1H-indole-2-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/156165,2017,A1

12
[ 261762-56-5 ]
4-chloro-5-fluoro-6-methoxy-1-methyl-1H-indole-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2017/156165,2017,A1

13
[ 261762-56-5 ]
2-chloro-3-fluoro-4-methoxybenzoic acid methyl ester [ No CAS ]

Reference： [1]Patent: WO2018/46684,2018,A1

14
[ 261762-56-5 ]
1-bromo-2-chloro-3-fluoro-4-methoxybenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With bromine; In chlorobenzene; at 5 - 25℃; for 9h;Inert atmosphere;	In a four-necked 250 mL round-bottomed flask, equipped with a thermometer, a reflux condenser with pressure equalizer, a dry ice cooled dropping funnel (-30 C) and a gas inlet, 50.0 g (purity 97.0 w%, 302 mmol, 1.0 eq) of l-chloro-2-fluoro-3-methoxy-benzene (1, CAS- No. 261762-56-5) were dissolved in 70 mL of chlorobenzene. To the solution 53.1 g (purity 98.0 w%, 332 mmol, 1.1 eq) bromine was added over one hour at 5-10 C internal temperature via cooling externally at 0 C. After complete addition the reaction was allowed to reach 25 C. The reaction was continued for further 8 hours under a constant stream of nitrogen purge gas to remove HBr from the reaction mixture. Afterwards a HPLC measurement indicated >98% conversion. The reaction solution was then washed with 100 mL of aqueous saturated NaHC03 solution and 50 mL of deionized water. Afterwards the organic phase was dried over MgSC^, the drying agent was filtered off and the solvent was removed in vacuum at 65 C and 5 mbar to leave 72.6 g (90%, purity 90%) of a brownish solid. The solid was purified via vacuum distillation at 10 mbar and temperature of 118-122 C to yield 57.4 g (79%, purity 99%) of a white solid. NMR (CDC13, 400 MHz) delta (ppm) = 7.34 (dd, J= 8.0, 2.0 Hz, 1H), 6.79 (dd, J= 8.0, 8.0 Hz, 1H), 3.89 (s, 3H).

Reference： [1]Patent: WO2018/46684,2018,A1 .Location in patent: Page/Page column 75-76

15
[ 261762-56-5 ]
2-chloro-3-fluoro-4-methoxybenzoic acid [ No CAS ]

Reference： [1]Patent: WO2018/46684,2018,A1

16
[ 261762-56-5 ]
(2R,3S)-3-((4-chloro-2-(6-chloro-3-methoxyquinolin-8-yl)-5-fluorobenzo[d]thiazol-6-yl)oxy)butan-2-yl (2-(2-hydroxyethoxy)pyrimidin-5-yl)carbamate [ No CAS ]