[ CAS No. 102151-33-7 ] {[proInfo.proName]}

Name: 102151-33-7|3-Chloro-4-methoxybenzonitrile|96%
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SKU: A222902
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2D 3D

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Quality Control of [ 102151-33-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 102151-33-7 ]

SDS Specification

Alternatived Products of [ 102151-33-7 ]

Product Details of [ 102151-33-7 ]

CAS No. :	102151-33-7	MDL No. :	MFCD03093073
Formula :	C₈H₆ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SUFOLDHSHRVSQV-UHFFFAOYSA-N
M.W :	167.59	Pubchem ID :	4323105
Synonyms :

Calculated chemistry of [ 102151-33-7 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.66
TPSA :	33.02 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) :	-5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.99
Log Po/w (XLOGP3) :	2.25
Log Po/w (WLOGP) :	2.22
Log Po/w (MLOGP) :	1.71
Log Po/w (SILICOS-IT) :	2.43
Consensus Log Po/w :	2.12

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.63
Solubility :	0.389 mg/ml ; 0.00232 mol/l
Class :	Soluble
Log S (Ali) :	-2.58
Solubility :	0.441 mg/ml ; 0.00263 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.22
Solubility :	0.101 mg/ml ; 0.000603 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.5

Safety of [ 102151-33-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H317-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 102151-33-7 ]

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

Upstream synthesis route of [ 102151-33-7 ]
Downstream synthetic route of [ 102151-33-7 ]

[ 102151-33-7 ] Synthesis Path-Upstream 1~13

1
[ 102151-33-7 ]
[ 2315-81-3 ]

Yield	Reaction Conditions	Operation in experiment
3.17 g	With boron tribromide In dichloromethane at -78 - 20℃;	To a solution of 3-chloro-4-methoxybenzonitrile (4.25g) in DCM (85m1) was added a -78°C dropwise 1M BBr3 in DCM (50.7m1). The reaction mixture was stirred at -78°C for 10mm and at rt overnight. The mixture was then stirred at 40°C for 4.5d and additional BBr3 sol. (26m1) was added on the first, second and third day, respectively. The reaction mixture wascarefully quenched with water, the solid precipitate was filtrated off. The layers were separated, the aq. phase was washed with DCM and the combined org. layers were dried over MgSO4, filtrated off and evaporated in vacuo. The crude was purified by CC (Büchi Sepacore, 50g cartridge, solvent A: Heptane, solvent B: EA, gradient in percentB: 0 to 40, flow rate: 30 mI/mm) to afford 3.17g of a brown oil. LC-MS (A): tR = 0.68 mm; [M+H]: not visible.
3.17 g	With boron tribromide In dichloromethane at -78 - 20℃; Inert atmosphere	To a solution of 3-chloro-4-methoxybenzonitrile (4.25g) in DCM (85 mL) was added a -78°C dropwise 1 M sol. of BBr₃ in DCM (50.7 mL). The reaction mixture was stirred at -78°C for 10 min and at RT overnight. The mixture was then stirred at 40°C for 4.5d and additional BBr₃ sol. (26 mL) was added on the first, second and third day respectively. The reaction mixture was carefully quenched with water, the solid precipitate was filtrated off. The layers were separated, the aq. phase was washed with DCM and the combined org. layers were dried over MgS0₄, filtrated off and evaporated in vacuo. The crude was purified by CC (Buchi Sepacore, 50g cartridge, solvent A: Heptane , solvent B: EA, gradient in percentB: 0 to 40, flow rate: 30 mL/min) to afford 3.17g of a brown oil. LC-MS (A): t_R = 0.68 min; [M+H]⁺: not visible.

Reference： [1] Patent: WO2015/75025, 2015, A1, . Location in patent: Page/Page column 93
[2] Patent: WO2015/75023, 2015, A1, . Location in patent: Page/Page column 139

2
[ 2315-81-3 ]
[ 74-88-4 ]
[ 102151-33-7 ]

Reference： [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 6, p. 1065 - 1080
[2] Patent: US4642311, 1987, A,
[3] Patent: US4853383, 1989, A,
[4] Patent: WO2011/109799, 2011, A1, . Location in patent: Page/Page column 124

3
[ 55305-43-6 ]
[ 5345-54-0 ]
[ 102151-33-7 ]

Reference： [1] Tetrahedron Letters, 2016, vol. 57, # 11, p. 1205 - 1209

4
[ 137042-63-8 ]
[ 102151-33-7 ]

Reference： [1] Chemical Communications, 2013, vol. 49, # 30, p. 3146 - 3148

5
[ 7677-24-9 ]
[ 766-51-8 ]
[ 102151-33-7 ]

Reference： [1] Journal of the American Chemical Society, 2017, vol. 139, # 8, p. 2880 - 2883

6
[ 874-90-8 ]
[ 102151-33-7 ]

Reference： [1] Chemical Science, 2017, vol. 8, # 10, p. 7009 - 7013

7
[ 37908-98-8 ]
[ 102151-33-7 ]

Reference： [1] Journal of Pharmaceutical Sciences, 1986, vol. 75, # 4, p. 410 - 412

8
[ 67-56-1 ]
[ 117482-84-5 ]
[ 102151-33-7 ]

Reference： [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 11, p. 1634 - 1647

9
[ 89978-93-8 ]
[ 102151-33-7 ]

Reference： [1] Journal of Pharmaceutical Sciences, 1986, vol. 75, # 4, p. 410 - 412

10
[ 37908-96-6 ]
[ 102151-33-7 ]

Reference： [1] Journal of Pharmaceutical Sciences, 1986, vol. 75, # 4, p. 410 - 412

11
[ 36590-49-5 ]
[ 102151-33-7 ]

Reference： [1] Journal of Pharmaceutical Sciences, 1986, vol. 75, # 4, p. 410 - 412

12
[ 4920-79-0 ]
[ 143-33-9 ]
[ 10496-75-0 ]
[ 102151-33-7 ]

Reference： [1] Organic Letters, 2007, vol. 9, # 15, p. 2803 - 2806
[2] Organic Letters, 2007, vol. 9, # 15, p. 2803 - 2806

13
[ 4920-79-0 ]
[ 143-33-9 ]
[ 1007122-94-2 ]
[ 10496-75-0 ]
[ 102151-33-7 ]

Reference： [1] Journal of Organic Chemistry, 2008, vol. 73, # 5, p. 1925 - 1934

[ 102151-33-7 ] Synthesis Path-Downstream 1~41

1
[ 67-56-1 ]
[ 102151-33-7 ]
[ 102151-34-8 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1065 - 1080

2
[ 89978-93-8 ]
[ 102151-33-7 ]

Reference： [1]Journal of Pharmaceutical Sciences,1986,vol. 75,p. 410 - 412

3
[ 925-90-6 ]
[ 102151-33-7 ]
[ 4394-54-1 ]

Reference： [1]Journal of Pharmaceutical Sciences,1986,vol. 75,p. 410 - 412

4
[ 2315-81-3 ]
[ 74-88-4 ]
[ 102151-33-7 ]

Yield	Reaction Conditions	Operation in experiment
	In water; N,N-dimethyl-formamide;	Step A 3-Chloro-4-methoxybenzonitrile (26) Under N2, a solution of 3-chloro-4-hydroxybenzonitrile (15.4 g, 0.1 mole) in dry DMF (75 ml) was added rapidly dropwise to a stirred suspension of sodium hydride (4.0 g, 0.1 mole, 60% oil dispersion) in dry DMF (25 ml). After heating at 70 C. for 2 hours, the mixture was cooled to 20 C. and a solution of methyliodide (30 ml) in dry DMF (50 ml) was added dropwise. Following an 18 hour period at room temperature, the precipitate of sodium iodide was removed by filtration and the solvent was stripped from the filtrate under reduced pressure. The crystalline residue was slurried in water and the product was collected to yield 16.8 g (quant.) of 26, m.p. 105-108 C.
	In water; N,N-dimethyl-formamide;	Step A: 3-Chloro-4-methoxybenzonitrile (26) Under N2, a solution of 3-chloro-4-hydroxybenzonitrile (15.4 g, 0.1 mole) in dry DMF (75 ml) was added rapidly dropwise to a stirred suspension of sodium hydride (4.0 g, 0.1 mole, 60% oil dispersion) in dry DMF (25 ml). After heating at 70 C. for 2 hours, the mixture was cooled to 20 C. and a solution of methyliodide (30 ml) in dry DMF (50 ml) was added dropwise. Following an 18 hour period at room temperature, the precipitate of sodium iodide was removed by filtration and the solvent was stripped from the filtrate under reduced pressure. The crystalline residue was slurried in water and the product was collected to yield 16.8 g (quant.) of 26, m.p. 105-108 C.
	With potassium carbonate; In acetone; at 20℃;	Synthesis of Intermediate (1)[00334] In a 3-neck 100 mL round-bottomed flask, 3 -Chloro-5 -hydroxy benzonitrile (3.5 g, 1 eq.) was mixed with potassium carbonate (4.71 g, 1.5 eq.) using acetone (70 mL, 20 Vol.) as solvent. To this reaction mixture methyl Iodide (6.46 g, 2.0 eq.) was added drop-wise at room temperature and reaction was further stirred at RT for 3-4 h. Reaction completion was monitored on TLC using ethyl acetate: n-hexane (2:8) mobile phase. The reaction mixture was quenched into ice-water slurry (150 mL) and compound was extracted in the ethyl acetate (50 mol x 3). Organic layer was washed with brine solution (50 mol x 3) followed by drying using anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure to afford 3.5 g of crude compound, Yield (92.1 %).

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1065 - 1080
[2]Patent: US4642311,1987,A
[3]Patent: US4853383,1989,A
[4]Patent: WO2011/109799,2011,A1 .Location in patent: Page/Page column 124

5
[ 67-56-1 ]
[ 117482-84-5 ]
[ 102151-33-7 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1634 - 1647

6
[ 5470-49-5 ]
[ 102151-33-7 ]
[ 189297-37-8 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1634 - 1647

7
[ 4920-79-0 ]
[ 143-33-9 ]
C₇H₅ClONCNO₂⁽²⁾H^(1-) [ No CAS ]
[ 10496-75-0 ]
[ 102151-33-7 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 2803 - 2806
[2]Organic Letters,2007,vol. 9,p. 2803 - 2806

8
[ 102151-33-7 ]
[ 177661-25-5 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1634 - 1647

9
[ 102151-33-7 ]
4-[2-(3-chloro-4-methoxyphenyl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1634 - 1647

10
[ 102151-33-7 ]
[ 177661-55-1 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1634 - 1647

11
[ 37908-96-6 ]
[ 102151-33-7 ]

Reference： [1]Journal of Pharmaceutical Sciences,1986,vol. 75,p. 410 - 412

12
[ 37908-98-8 ]
[ 102151-33-7 ]

Reference： [1]Journal of Pharmaceutical Sciences,1986,vol. 75,p. 410 - 412

13
[ 36590-49-5 ]
[ 102151-33-7 ]

Reference： [1]Journal of Pharmaceutical Sciences,1986,vol. 75,p. 410 - 412

14
[ 102151-33-7 ]
[ 102976-53-4 ]

Reference： [1]Journal of Pharmaceutical Sciences,1986,vol. 75,p. 410 - 412

15
[ 102151-33-7 ]
(+/-)-2-tert-butylamino-3'-chloro-4'-methoxypropiophenone [ No CAS ]

Reference： [1]Journal of Pharmaceutical Sciences,1986,vol. 75,p. 410 - 412

16
[ 102151-33-7 ]
[ 102151-35-9 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1065 - 1080

17
[ 5470-49-5 ]
[ 75-24-1 ]
[ 102151-33-7 ]
[ 189297-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane; chloroform; toluene;	Step 1 Preparation of 3-chloro-4-methoxy-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide To a suspension of 4-(methylsulfonyl)aniline (10 mmol) in toluene (100 mL), trimethylaluminum (2M solution in toluene, 15 mmol) is added over 15 minutes. The reaction mixture is warmed to room temperature and stirred for 2.5 hours. A solution of <strong>[102151-33-7]3-chloro-4-methoxybenzonitrile</strong> (20 mmol) in toluene (50 mL) is added over 10 minutes and the reaction mixture is heated to 80-85 C. After 20 hours, the reaction mixture is cooled to room temperature and poured over a slurry of silica gel in chloroform. After filtration, the residue is washed with a mixture of methylene chloride/methanol (2/1). The combined filtrates are concentrated in vacuo and the resulting yellowish solid is stirred with a mixture of hexane/ether (2/1, 1000 mL).

Reference： [1]Patent: US5616601,1997,A

18
iron(III) chloride [ No CAS ]
N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride [ No CAS ]
[ 102151-33-7 ]
[ 168010-83-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; ammonia; In 1,2-dichloro-benzene;	Reference Example 6 Preparation of 3-(2-chloro-6-fluorophenyl)-5-(3-chloro-4-hydroxyphenyl) 1-methyl-1H-1,2,4-triazole To o-dichlorobenzene (200 ml) are added <strong>[102151-33-7]3-chloro-4-methoxybenzonitrile</strong> (40.3 g) and anhydrous iron (III) chloride (42.2 g), which are heated at 120 C. with stirring. To this mixture is added dropwise a solution of N-methyl-N-(p-toluenesulfonyl)-2-chloro-6-fluorobenzohydrazonoyl chloride (62.2 g) in o-dichlorobenzene (300 ml) at 120 C. for 30 minutes with stirring, which are further stirred at 120 C. for 3 hours. After cooling to room temperature, the reaction mixture is poured into a large amount of water and extracted with chloroform. The organic layer is added with aqueous solution of 10% NaOH (200 ml) and aqueous solution of 25% ammonia (200 ml) and stirred at 50 C. for 1 hour. After cooling to room temperature, the organic layer is washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure to give 70.5 g of a crude product of 3-(2-chloro-6-fluorophenyl)-5-(3-chloro-4-methoxyphenyl) 1-methyl-1H-1,2,4-triazole.

Reference： [1]Patent: US5616594,1997,A

19
[ 102151-33-7 ]
[ 102151-34-8 ]
3-chloro-4-methoxybenzimidamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In methanol; CH3 OH (6 ml)-dioxane; diethyl ether;	Step B 3-Chloro-4-methoxybenzamidine hydrochloride (27) Under N2, a stirred suspension of 26 (16.1 g, 0.096 mole) in CH3 OH (6 ml)--dioxane (20 ml) was cooled in an ice bath and saturated with gaseous HCl. The resulting mixture was refrigerated. After 3 days, the solid mass was suspended in Et2 O and the methyl 3-chloro-4-methoxybenzimidate hydrochloride was collected to afford 17.5 g (77%), m.p. 190-192 C. Methyl 3-chloro-4-methoxybenzimidate hydrochloride, (19.9 g, 0.084 mole) was added to a solution of ammonia (12 g) in CH3 OH (100 ml) cooled to -78 C. The stirred mixture was allowed to warm to room temperature. After 20 hours, the solution was evaporated to dryness under reduced pressure. The solid residue was triturated with Et2 O and collected to yield 17.8 g (96%) of 27, m.p. dec. 243-245 C. A sample triturated with acetone melted at 241-243 C. dec. Analysis calculated for C8 H10 Cl2 N2 O: C, 43.46; H, 4.56, N, 12.67. Found: C, 42.84; H, 4.83; N, 12.74.
	With ammonia; In methanol; CH3 OH (6 ml)-dioxane; diethyl ether;	Step B: 3-Chloro-4-methoxybenzamidine hydrochloride (27) Under N2, a stirred suspension of 26 (16.1 g, 0.096 mole) in CH3 OH (6 ml)--dioxane (20 ml) was cooled in an ice bath and saturated with gaseous HCl. The resulting mixture was refrigerated. After 3 days, the solid mass was suspended in Et2 O and the methyl 3-chloro-4-methoxybenzimidate hydrochloride was collected to afford 17.5 g (77%), m.p. 190-192 C. Methyl 3-chloro-4-methoxybenzimidate hydrochloride, (19.9 g, 0.084 mole) was added to a solution of ammonia (12 g) in CH3 OH (100 ml) cooled to -78 C. The stirred mixture was allowed to warm to room temperature. After 20 hours, the solution was evaporated to dryness under reduced pressure. The solid residue was triturated with Et2 O and collected to yield 17.8 g (96%) of 27, m.p. dec. 243-245 C. A sample triturated with acetone melted at 241-243 C. dec.

Reference： [1]Patent: US4642311,1987,A
[2]Patent: US4853383,1989,A

20
[ 4920-79-0 ]
[ 143-33-9 ]
[ 1007122-94-2 ]
[ 10496-75-0 ]
[ 102151-33-7 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 1925 - 1934

22
[ 102151-33-7 ]
[ 1333151-61-3 ]

Reference： [1]Patent: WO2011/109799,2011,A1

23
[ 64-18-6 ]
[ 102151-33-7 ]
[ 1333152-96-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate; In N,N-dimethyl-formamide; at 90℃; for 12h;	Synthesis of Intermediate (2)[00336] In a 3-neck 50 mL round-bottomed flask, Intermediate- 1 (3.5 g, 1 eq.) was dissolved in DMF (70 mL, 20 Vol.). Formic acid (18 mL, 5.1 Vol.) and Hydrazine hydrate (18 mL, 5.1 Vol.) was added to this reaction mixture. Reaction mixture was refluxed to 90 C for 12 h. Reaction completion was monitored on TLC using ethyl acetate: n-hexane (5:5) as mobile phase. Reaction mixture was brought to room temperature after completion and quenched into the ice- water slurry (350 mL) and compound was extracted in the Ethyl acetate (100 mL x 3). Organic layer was washed with brine solution (100 mL x 3) followed by drying using anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure to afford 4.0 g of crude compound. Compound was purified by column chromatography using silica 60/120 and ethylacetate: hexane as mobile phase. Column purification was started with 5 % EtOAc in hexane up to 30 % EtOAc. Compound started eluting in 25 % ethylacetate and continued till 30 % EtOAc. Fractions containing compound was distilled out using rotary evaporation at 45 C / 250 mm Hg to obtain 0.7 g of pure compound, Yield (16.2%).

Reference： [1]Patent: WO2011/109799,2011,A1 .Location in patent: Page/Page column 124-125

24
[ 90359-73-2 ]
[ 102151-33-7 ]
[ 1409950-48-6 ]

Reference： [1]Patent: US2013/115190,2013,A1
[2]Patent: US9527885,2016,B2

25
[ 90359-73-2 ]
[ 102151-33-7 ]
[ 1409950-49-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With tert.-butyl lithium; In tetrahydrofuran; pentane;	Step 1 To a solution of N,N-diethyl-4-methoxy-2-methylbenzamide (1 g, 4.52 mmol) in THF (9 ml) at -78 C. was added dropwise tert-butyllithium 1.7 M in pentane (3.19 ml, 5.42 mmol) and the solution was stirred for 0.5 h before addition of <strong>[102151-33-7]3-chloro-4-methoxybenzonitrile</strong> (0.757 g, 4.52 mmol) in THF (9 ml). The resulting solution was warmed to rt and stirred for 16 h. The reaction mixture was quenched with water, neutralized with 1 N HCl. The precipitated solid was collected and washed with water to give 3-(3-chloro-4-methoxyphenyl)-6-methoxyisoquinolin-1-ol (1.2 g, 84% yield) as a solid after drying. MS: MS m/z 316.1 (M++1).
84%		To a solution of N,N-diethyl-4-methoxy-2-methylbenzamide (1 g, 4.52 mmol) in THF (9 ml) at -78 C. was added dropwise tert-butyllithium 1.7 M in pentane (3.19 ml, 5.42 mmol) and the solution was stirred for 0.5 h before addition of <strong>[102151-33-7]3-chloro-4-methoxybenzonitrile</strong> (0.757 g, 4.52 mmol) in THF (9 ml). The resulting solution was warmed to rt and stirred for 16 h. The reaction mixture was quenched with water, neutralized with 1 N HCl. The precipitated solid was collected and washed with water to give 3-(3-chloro-4-methoxyphenyl)-6-methoxyisoquinolin-1-ol (1.2 g, 84% yield) as a solid after drying. MS: MS m/z 316.1 (M++1)

Reference： [1]Patent: US2013/115190,2013,A1 .Location in patent: Page/Page column
[2]Patent: US9527885,2016,B2 .Location in patent: Page/Page column 46

26
[ 137042-63-8 ]
[ 102151-33-7 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 3146 - 3148

27
2-chloro-4-ethynyl-1-methoxybenzene [ No CAS ]
[ 102151-33-7 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 6677 - 6680
Angew. Chem.,2013,vol. 125,p. 6809 - 6612,4

28
[ 102151-33-7 ]
[ 2315-81-3 ]

Yield	Reaction Conditions	Operation in experiment
3.17 g	With boron tribromide; In dichloromethane; at -78 - 20℃;	To a solution of <strong>[102151-33-7]3-chloro-4-methoxybenzonitrile</strong> (4.25g) in DCM (85m1) was added a -78C dropwise 1M BBr3 in DCM (50.7m1). The reaction mixture was stirred at -78C for 10mm and at rt overnight. The mixture was then stirred at 40C for 4.5d and additional BBr3 sol. (26m1) was added on the first, second and third day, respectively. The reaction mixture wascarefully quenched with water, the solid precipitate was filtrated off. The layers were separated, the aq. phase was washed with DCM and the combined org. layers were dried over MgSO4, filtrated off and evaporated in vacuo. The crude was purified by CC (Buechi Sepacore, 50g cartridge, solvent A: Heptane, solvent B: EA, gradient in %B: 0 to 40, flow rate: 30 mI/mm) to afford 3.17g of a brown oil. LC-MS (A): tR = 0.68 mm; [M+H]: not visible.
3.17 g	With boron tribromide; In dichloromethane; at -78 - 20℃;Inert atmosphere;	To a solution of <strong>[102151-33-7]3-chloro-4-methoxybenzonitrile</strong> (4.25g) in DCM (85 mL) was added a -78C dropwise 1 M sol. of BBr3 in DCM (50.7 mL). The reaction mixture was stirred at -78C for 10 min and at RT overnight. The mixture was then stirred at 40C for 4.5d and additional BBr3 sol. (26 mL) was added on the first, second and third day respectively. The reaction mixture was carefully quenched with water, the solid precipitate was filtrated off. The layers were separated, the aq. phase was washed with DCM and the combined org. layers were dried over MgS04, filtrated off and evaporated in vacuo. The crude was purified by CC (Buchi Sepacore, 50g cartridge, solvent A: Heptane , solvent B: EA, gradient in %B: 0 to 40, flow rate: 30 mL/min) to afford 3.17g of a brown oil. LC-MS (A): tR = 0.68 min; [M+H]+: not visible.

Reference： [1]Patent: WO2015/75025,2015,A1 .Location in patent: Page/Page column 93
[2]Patent: WO2015/75023,2015,A1 .Location in patent: Page/Page column 139

29
[ 102151-33-7 ]
methyl 2-(2-chloro-4-cyanophenoxy)acetate [ No CAS ]

Reference： [1]Patent: WO2015/75025,2015,A1

30
[ 102151-33-7 ]
2-(2-chloro-4-cyanophenoxy)acetic acid [ No CAS ]

Reference： [1]Patent: WO2015/75025,2015,A1

31
[ 55305-43-6 ]
[ 5345-54-0 ]
[ 102151-33-7 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: In an Erlenmeyer flask, the aniline (10.0 mmol) was dissolved in an aqueous solution of H4BF4 (50%, 5.0 mL,40.0 mmol) and a saturated solution of sodium nitrite (760 mg, 11.0 mmol) was added dropwise at 0 C. The excess oxidant was removed by the addition of urea. Then, the precipitated diazonium salt was filtered off and dissolved in a small amount of acetone. Diethyl ether was added to the clear solution, causing the precipitation of the arenediazonium tetrafluoroborate, which was filtered off and washed with diethyl ether (3×10.0 mL). The arenediazonium tetrafluoroborate was dried in vacuo (10-3 mbar) for 10 minutes and was then directly used without further purification. (II) General synthesis of N-cyano-N-phenyl-p-methylbenzenesulfonamide(NCTS): (see reference 2) Dry 250 ml Schlenk flask was a solution of phenylurea (10.9 g, 8 mmol) in pyridine (54 mL). The flask was stirred in room temperature water bath. p-Toluenesulfonylchloride (52.8 g, 27.7 mmol) was added potion wise over 5 minutes. The reaction mixture was stirred for another additional 20 minutes and poured into to ice-cooled water (400 mL) with mechanical stirring. Precipitate formed during mechanical stirring was filtered and then washed with water. The crude product was treated with 50 ml of ethanol and precipitated from the same solvent. The precipitate was purified with column chromatography using heptane:EtOAc (15:1) as eluent to yield N-cyano-N-phenyl-p-methylbenzenesulfonamide as colorless solid (16.5 g, 76%). (III) General synthesis of aryl nitriles from the corresponding arenediazonium salts. To a solution of arenediazonium tetrafluoroborate (0.5 mmol) in EtOH (3.0 mL) was added NCTS (272 mg, 1.0 mmol), Pd(OAc)2 (16.8 mg, 0.075 mmol), Ag2CO3 (68.7mg, 0.25 mmol). The mixture was stirred at 58 for 15 h under air atmosphere. Then the reaction mixture was cooled to room temperature and filtered through a pad of celite (1.0 g) and rinsed with CH2Cl2 (10.0 mL). The resulting organic solution was concentrated under reduced pressure and further purified by flash chromatography (SiO2, petroleum ether/EtOAc gradient), yielding the corresponding aryl nitriles.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 1205 - 1209

32
[ 102151-33-7 ]
3-chloro-N'-hydroxy-4-methoxybenzenecarboximidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With hydroxylamine hydrochloride; triethylamine; In ethanol; at 50℃; for 16h;	To a solution of <strong>[102151-33-7]3-chloro-4-methoxybenzonitrile</strong> (500 mg, 3.30 mmol) in 10 ml ethanol was added hydroxylammonium chloride (311 mg, 4.0 mmol) and triethylamine (392 mg, 4.0 mmol) and then the reaction mixture was stirred 16 h at 50 C. After cooling to RT, the solvent was evaporated and the crude - - was solved in ethyl acetate and dichloromethane and extracted with water. The organic phase was dried over magnesium sulfate, filtered and evaporated under vacuum to yield the title compound (124 mg, 19 % of theory). LC-MS (method 3B): RT = 0.79 min, m/z = 201 (M+H)+

Reference： [1]Patent: WO2016/71216,2016,A1 .Location in patent: Page/Page column 205-206

33
[ 102151-33-7 ]
tert-butyl 4-{3-[3-(3-chloro-4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidin-7-yl}piperidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/71216,2016,A1

34
[ 7677-24-9 ]
[ 766-51-8 ]
[ 102151-33-7 ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 2880 - 2883

35
[ 874-90-8 ]
[ 102151-33-7 ]

Reference： [1]Chemical Science,2017,vol. 8,p. 7009 - 7013

36
[ 330660-35-0 ]
[ 766-51-8 ]
3-chloro-2-methoxylbenzonitrile [ No CAS ]
[ 102151-33-7 ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 2199 - 2202

37
[ 75-84-3 ]
[ 102151-33-7 ]
3-chloro-4-(neopentyloxy)benzonitrile [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 6077 - 6081

38
[ 102151-33-7 ]
[ 41965-95-1 ]

Reference： [1]Inorganic Chemistry,2019,vol. 58,p. 11274 - 11278

39
[ 67-56-1 ]
[ 102151-33-7 ]
3-chloro-4-methoxy-N-methylbenzamide [ No CAS ]

Reference： [1]ACS Catalysis,2019,vol. 9,p. 10469 - 10476

40
[ 86164-70-7 ]
[ 50638-47-6 ]
[ 102151-33-7 ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 19257 - 19262

41
[ 3964-56-5 ]
[ 102151-33-7 ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 19257 - 19262

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H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
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H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 102151-33-7 ] {[proInfo.proName]}

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[ 102151-33-7 ] Synthesis Path-Upstream 1~13

[ 102151-33-7 ] Synthesis Path-Downstream 1~41

Related Functional Groups of [ 102151-33-7 ]

Aryls

Chlorides

Nitriles

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Environmental hazards

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[ 102151-33-7 ]