[ CAS No. 16220-95-4 ]

Name: 16220-95-4|Methyl 2-chloro-5-methylbenzoate|98%
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Product Details of [ 16220-95-4 ]

CAS No. :	16220-95-4	MDL No. :	MFCD12025214
Formula :	C₉H₉ClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	184.62 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 16220-95-4 ]

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 [ 16220-95-4 ]

* 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 [ 16220-95-4 ]

[ 16220-95-4 ] Synthesis Path-Downstream 1~31

1
[ 6342-60-5 ]
[ 16220-95-4 ]

Reference： [1]Journal of Medicinal Chemistry,1967,vol. 10,p. 478 - 481

2
[ 16220-95-4 ]
[ 16220-99-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide;dibenzoyl peroxide; In tetrachloromethane;Reflux;	A mixture of methyl 2-chloro-5-methylbenzoate (3.Og, 16.2 mmol), N- bromosuccinimide (3.O g, 17.0 mmol), and benzoyl peroxide (catalytic) in anhydrous carbon tetrachloride (50 mL) was stirred at reflux overnight. Dichloromethane (50 mL) was added after cooling to room temperature. The mixture was extracted with 1 N NaOH (2 x 100 mL). The organic layer was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording methyl 5-(bromomethyl)-2-chlorobenzoate (4.06 g, 95% yield). The product was used without further purification.
	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;	General procedure: Corresponding 2-chloro-methylphenyl compounds (1 mmol) and PBO (0.1 mmol ) were dissolved in 5 mL CCl4, then NBS (1.1 mmol) was added slowly. The reaction was stirred at room temperature and monitored by TLC and cooled to room temperature upon completion of the reaction. The precipitated solid was filtrated and the filtrate was concentrated to give an oily liquid, which was directly subjected to a further reaction with Cs2CO3 (1.5 mmol) in 5 mL of CH3CN, and corresponding Schiff base (1 mmol) in dissolved CH3CN was added dropwise at room temperature. The solution was stirred at room temperature and monitored by TLC. Upon completion of the reaction, CH3CN was distilled off under reduced pressure and the residue was extracted CH2Cl2 (203 mL). Organic layer was dried over anhydrous Na2SO4, filtrated and concentrated under reduced pressure. The residue was purified by silica gel column to give the targeted compound.

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 3189 - 3202
[2]Journal of Medicinal Chemistry,1967,vol. 10,p. 478 - 481
[3]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4416 - 4420
[4]Patent: WO2010/132999,2010,A1 .Location in patent: Page/Page column 115
[5]Chinese Chemical Letters,2019,p. 255 - 258

3
[ 16220-95-4 ]
[ 1068-90-2 ]
[ 16277-18-2 ]

Yield	Reaction Conditions	Operation in experiment
	(i) NBS, (PhCO)2O₂, CCl₄, (ii) /BRN= 783883/, NaOEt, EtOH; Multistep reaction;

Reference： [1]Leonard,F. et al. [Journal of Medicinal Chemistry, 1967, vol. 10, p. 478 - 481]

Yield	Reaction Conditions	Operation in experiment
	2-Chlor-5-methylbenzoesaeure (VI), MeOH;
	Saeure (I), Me./H2SO4;

5
[ 73129-52-9 ]
[ 16220-95-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaOBr 2: (esterification)

Reference： [1]Leonard,F. et al. [Journal of Medicinal Chemistry, 1967, vol. 10, p. 478 - 481]

6
[ 16220-95-4 ]
[ 13406-46-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (i) NBS, (PhCO)2O₂, CCl₄, (ii) /BRN= 783883/, NaOEt, EtOH 2: aq. HCl

Reference： [1]Leonard,F. et al. [Journal of Medicinal Chemistry, 1967, vol. 10, p. 478 - 481]

7
[ 79-37-8 ]
[ 6342-60-5 ]
[ 16220-95-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	In methanol; dichloromethane; N,N-dimethyl-formamide;	Example 83 6-(2-CHLORO-5-METHYL-PHENYL)-N-(4-CHLORO-PHENYL)-[1,3,5]TRIAZINE-2,4-DIAMINE To a suspension of <strong>[6342-60-5]2-chloro-5-methyl-benzoic acid</strong> (3.0 g, 17.6 mmol) in dichloromethane (50 ml) was added a solution of oxalyl chloride in dichloromethane (2 M, 10 ml, 20 mmol) followed by N,N-dimethylformamide (5 drops). After stirring for 1 hour, methanol (20 ml) was added. After stirring for 3 hours, the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (200 ml) and saturated aqueous potassium carbonate solution (100 ml). The organic layer was concentrated under reduced pressure to provide methyl 2-chloro-5-methyl-benzoate (3.2 g, 100% yield).

Reference： [1]Patent: US2003/153570,2003,A1

8
[ 18595-16-9 ]
[ 16220-95-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; copper(l) chloride; sodium nitrite In water at 0 - 5℃;

Reference： [1]Location in patent: scheme or table Chang, Dong-Jo; Yoon, Eun-Young; Lee, Geon-Bong; Kim, Soon-Ok; Kim, Wan-Joo; Kim, Young-Myeong; Jung, Jong-Wha; An, Hongchan; Suh, Young-Ger [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 15, p. 4416 - 4420]

9
[ 67-56-1 ]
[ 6342-60-5 ]
[ 16220-95-4 ]

Yield	Reaction Conditions	Operation in experiment
	sulfuric acid; for 5h;Reflux;	A mixture of <strong>[6342-60-5]2-chloro-5-methylbenzoic acid</strong> (4.0 g, 23.4 mmol) in methanol (50 niL) and a few drops of concentrated sulfuric acid were stirred at reflux for 5 hours. After cooling to room temperature, methanol was evaporated. The residue was dissolved in ethyl acetate (50 mL). The solution was extracted with saturated NaHCO3 (3 x 50 mL). The organic layer was dried over MgSO4, filtered, evaporated, and dried in vacuo, affording methyl 2-chloro-5-methylbenzoate (3.07g, 71% yield). The product was used without further purification.
	With sulfuric acid; for 20h;Reflux;	A solution of 2- chloro-5-methylbenzoic acid (5g, 29.3 immol, 1 equiv.) in MeOH (60 mL) was added with concentrated H2S04 (1 mL), the mixture was refluxed for 20 h. Then cooled toroom temperature and concentrated to remove most of MeOH, the residue was diluted with water and extracted with CH2C12, dried over Na2SO4, concentrated and purified via FCC (Hexanes: EtOAc, 10:1) to give product methyl 2-chloro-5-methylbenzoate as grey solid. A solution of above obtained methyl 2-chloro-5-methylbenzoate in CC14 (60 mL) was added with NBS (13g, 2.5 equiv.) and benzoyl peroxide (5 mol%,0.4g), the mixture was stirred at reflux condition for 48 h, then cooled to room temperature and filtered, the filtrated was collected and concentrated. The cmde product was diluted with Et20 and filtered again, the filtrate was collect and concentrated, which was used for next step without purification.

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 3189 - 3202
[2]Organic Letters,2013,vol. 15,p. 3698 - 3701
[3]Patent: WO2010/132999,2010,A1 .Location in patent: Page/Page column 115
[4]Chinese Chemical Letters,2019,p. 255 - 258
[5]Patent: WO2019/18718,2019,A1 .Location in patent: Page/Page column 44

10
[ 16220-95-4 ]
2-chloro-N-(1-(cyclopropylmethyl)pyrrolidin-3-yl)-5-((2,4-dioxo-3,4-dihydroquinazoline-1(2H)-yl)methyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile; tetrachloromethane / Reflux 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; sulfuric acid / toluene / Inert atmosphere 2.2: Inert atmosphere; Heating 2.3: 70 - 100 °C / Inert atmosphere 3.1: lithium hydroxide / methanol; water; tetrahydrofuran / 0.92 h / Heating 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

Reference： [1]Zhou, Jie; Ji, Ming; Yao, Haiping; Cao, Ran; Zhao, Hailong; Wang, Xiaoyu; Chen, Xiaoguang; Xu, Bailing [Organic and Biomolecular Chemistry, 2018, vol. 16, # 17, p. 3189 - 3202]

11
[ 16220-95-4 ]
3-(2-chloro-5-((2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)methyl)benzoylamino)pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile; tetrachloromethane / Reflux 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; sulfuric acid / toluene / Inert atmosphere 2.2: Inert atmosphere; Heating 2.3: 70 - 100 °C / Inert atmosphere 3.1: lithium hydroxide / methanol; water; tetrahydrofuran / 0.92 h / Heating 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

Reference： [1]Zhou, Jie; Ji, Ming; Yao, Haiping; Cao, Ran; Zhao, Hailong; Wang, Xiaoyu; Chen, Xiaoguang; Xu, Bailing [Organic and Biomolecular Chemistry, 2018, vol. 16, # 17, p. 3189 - 3202]

12
[ 16220-95-4 ]
2-chloro-5-((2,4-dioxo-3,4-dihydroquinazoline-1(2H)-yl)methyl)-N-(pyrrolidin-3-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile; tetrachloromethane / Reflux 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; sulfuric acid / toluene / Inert atmosphere 2.2: Inert atmosphere; Heating 2.3: 70 - 100 °C / Inert atmosphere 3.1: lithium hydroxide / methanol; water; tetrahydrofuran / 0.92 h / Heating 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 20 °C

Reference： [1]Zhou, Jie; Ji, Ming; Yao, Haiping; Cao, Ran; Zhao, Hailong; Wang, Xiaoyu; Chen, Xiaoguang; Xu, Bailing [Organic and Biomolecular Chemistry, 2018, vol. 16, # 17, p. 3189 - 3202]

13
[ 16220-95-4 ]
2-chloro-5-((2,4-dioxo-3,4-dihydroquinazoline-1(2H)-yl)methyl)benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile; tetrachloromethane / Reflux 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; sulfuric acid / toluene / Inert atmosphere 2.2: Inert atmosphere; Heating 2.3: 70 - 100 °C / Inert atmosphere

Reference： [1]Zhou, Jie; Ji, Ming; Yao, Haiping; Cao, Ran; Zhao, Hailong; Wang, Xiaoyu; Chen, Xiaoguang; Xu, Bailing [Organic and Biomolecular Chemistry, 2018, vol. 16, # 17, p. 3189 - 3202]

14
[ 16220-95-4 ]
2-chloro-N-(1-(4,4-difluorocyclohexyl)pyrrolidin-3-yl)-5-((2,4-dioxo-3,4-dihydroquinazoline-1(2H)-yl)methyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile; tetrachloromethane / Reflux 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; sulfuric acid / toluene / Inert atmosphere 2.2: Inert atmosphere; Heating 2.3: 70 - 100 °C / Inert atmosphere 3.1: lithium hydroxide / methanol; water; tetrahydrofuran / 0.92 h / Heating 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 20 °C 6.1: sodium acetate / methanol; dichloromethane / 37 °C

Reference： [1]Zhou, Jie; Ji, Ming; Yao, Haiping; Cao, Ran; Zhao, Hailong; Wang, Xiaoyu; Chen, Xiaoguang; Xu, Bailing [Organic and Biomolecular Chemistry, 2018, vol. 16, # 17, p. 3189 - 3202]

15
[ 16220-95-4 ]
N-(1-benzylpyrrolidin-3-yl)-2-chloro-5-((2,4-dioxo-3,4-dihydroquinazoline-1(2H)-yl)methyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile; tetrachloromethane / Reflux 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; sulfuric acid / toluene / Inert atmosphere 2.2: Inert atmosphere; Heating 2.3: 70 - 100 °C / Inert atmosphere 3.1: lithium hydroxide / methanol; water; tetrahydrofuran / 0.92 h / Heating 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 20 °C 6.1: sodium acetate / methanol; dichloromethane / 37 °C

Reference： [1]Zhou, Jie; Ji, Ming; Yao, Haiping; Cao, Ran; Zhao, Hailong; Wang, Xiaoyu; Chen, Xiaoguang; Xu, Bailing [Organic and Biomolecular Chemistry, 2018, vol. 16, # 17, p. 3189 - 3202]

16
[ 16220-95-4 ]
[ 1401683-82-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile; tetrachloromethane / Reflux 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; sulfuric acid / toluene / Inert atmosphere 2.2: Inert atmosphere; Heating 2.3: 70 - 100 °C / Inert atmosphere 3.1: lithium hydroxide / methanol; water; tetrahydrofuran / 0.92 h / Heating

Reference： [1]Zhou, Jie; Ji, Ming; Yao, Haiping; Cao, Ran; Zhao, Hailong; Wang, Xiaoyu; Chen, Xiaoguang; Xu, Bailing [Organic and Biomolecular Chemistry, 2018, vol. 16, # 17, p. 3189 - 3202]

17
[ 16220-95-4 ]
(E)-N-(1-(4-chloro-3-(hydrazinecarbonyl)benzyl)imidazolidin-2-ylidene)nitramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane 2: caesium carbonate / acetonitrile / 20 °C 3: hydrazine hydrate / 0 - 50 °C

Reference： [1]Zhu, Chengchun; Li, Guanglong; Xiao, Keya; Shao, Xusheng; Cheng, Jiagao; Li, Zhong [Chinese Chemical Letters, 2019, p. 255 - 258]

18
[ 16220-95-4 ]
N-(4-chloro-3-(hydrazinecarbonyl)benzyl)-N'-cyano-N-methylacetimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane 2: caesium carbonate / acetonitrile / 20 °C 3: hydrazine hydrate / 0 - 50 °C

Reference： [1]Zhu, Chengchun; Li, Guanglong; Xiao, Keya; Shao, Xusheng; Cheng, Jiagao; Li, Zhong [Chinese Chemical Letters, 2019, p. 255 - 258]

19
[ 16220-95-4 ]
(E)-2-chloro-N-methyl-5-((2-(nitroimino)imidazolidin-1-yl)methyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane 2: caesium carbonate / acetonitrile / 20 °C 3: methanol / Reflux

Reference： [1]Zhu, Chengchun; Li, Guanglong; Xiao, Keya; Shao, Xusheng; Cheng, Jiagao; Li, Zhong [Chinese Chemical Letters, 2019, p. 255 - 258]

20
[ 16220-95-4 ]
2-chloro-5-((N'-cyano-N-methylacetimidamido)methyl)-N-methylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane 2: caesium carbonate / acetonitrile / 20 °C 3: methanol / Reflux

Reference： [1]Zhu, Chengchun; Li, Guanglong; Xiao, Keya; Shao, Xusheng; Cheng, Jiagao; Li, Zhong [Chinese Chemical Letters, 2019, p. 255 - 258]

21
[ 16220-95-4 ]
methyl (E)-2-chloro-5-((2-(nitroimino)imidazolidin-1-yl)methyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane 2: caesium carbonate / acetonitrile / 20 °C

Reference： [1]Zhu, Chengchun; Li, Guanglong; Xiao, Keya; Shao, Xusheng; Cheng, Jiagao; Li, Zhong [Chinese Chemical Letters, 2019, p. 255 - 258]

22
[ 16220-95-4 ]
methyl (E)-2-chloro-5-((N'-cyano-N-methylacetimidamido)methyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane 2: caesium carbonate / acetonitrile / 20 °C

Reference： [1]Zhu, Chengchun; Li, Guanglong; Xiao, Keya; Shao, Xusheng; Cheng, Jiagao; Li, Zhong [Chinese Chemical Letters, 2019, p. 255 - 258]

23
[ 16220-95-4 ]
methyl 2-chloro-5-(5-((4-methoxybenzo[d]thiazol-2-yl)amino)-1,3,4-oxadiazol-2-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 48 h / Reflux 1.2: 2 h / 50 °C 2.1: sodium dihydrogenphosphate; sodium chlorite / water; tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 20 °C 3.1: trichlorophosphate / 12 h / 90 °C / Inert atmosphere