448-36-2|2-Methoxy-4-(trifluoromethyl)benzoic acid| Ambeed

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Quality Control of [ 448-36-2 ] Purity: 98% SDS Specification

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Product Details of [ 448-36-2 ]

CAS No. :	448-36-2
Formula :	C₉H₇F₃O₃
M.W :	220.15
SMILES Code :	O=C(O)C1=CC=C(C(F)(F)F)C=C1OC
MDL No. :	MFCD04115976
Boiling Point :	No data available
InChI Key :	QWRIRBUKLBWVNF-UHFFFAOYSA-N
Pubchem ID :	3690873

Safety of [ 448-36-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 448-36-2 ]

* 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 [ 448-36-2 ]
Downstream synthetic route of [ 448-36-2 ]

[ 448-36-2 ] Synthesis Path-Upstream 1~1

1
[ 448-36-2 ]
[ 228572-69-8 ]

References: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 22, p. 6569 - 6584.

[ 448-36-2 ] Synthesis Path-Downstream 1~36

1
[ 54-96-6 ]
[ 448-36-2 ]
[ 95420-55-6 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 717 - 727.

2
[ 448-36-2 ]
[ 6638-79-5 ]
2,N-dimethoxy-N-methyl-4-trifluoromethyl-benzamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6569 - 6584.

3
[ 286441-66-5 ]
[ 448-36-2 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6569 - 6584.

4
[ 448-36-2 ]
2-{4-[3-(aminomethyl)phenoxy]-2-methylphenoxy}-2-methylpropanoic acid ester [ No CAS ]
2-(4-{3-[(2-methoxy-4-trifluoromethyl-benzoylamino)-methyl]-phenoxy}-2-methyl-phenoxy)-2-methyl-propionic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6744 - 6749.

5
[ 448-36-2 ]
1-[2-methoxy-4-(trifluoromethyl)phenyl]ethan-1-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6569 - 6584.

6
[ 448-36-2 ]
[ 915146-41-7 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6569 - 6584.

7
[ 448-36-2 ]
[ 915146-43-9 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6569 - 6584.

8
[ 448-36-2 ]
[ 915146-42-8 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6569 - 6584.

9
[ 448-36-2 ]
4-oxo-7-trifluoromethyl-4H-chromene-2-carboxylic acid (1-benzo[1,3]dioxol-5-ylmethyl-piperidin-4-yl)-amide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6569 - 6584.

10
[ 448-36-2 ]
[ 228572-69-8 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6569 - 6584.

11
[ 98-17-9 ]
[ 448-36-2 ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 2375.
[2]Journal of the American Chemical Society,1951,vol. 73,p. 2375.

12
[ 585-43-3 ]
[ 448-36-2 ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 2375.
[2]Journal of the American Chemical Society,1951,vol. 73,p. 2375.

13
[ 585-49-9 ]
[ 448-36-2 ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 2375.
[2]Journal of the American Chemical Society,1951,vol. 73,p. 2375.

14
[ 402-05-1 ]
[ 448-36-2 ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 2375.

15
[ 618-05-3 ]
[ 448-36-2 ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 2375.

Yield	Reaction Conditions	Operation in experiment
		Then, 0.20 g of the resulting tert-butyl N-5-[(2,4-dioxo-l,3-thiazolane-5-yl)methyl]-2-methoxybenzylamine hydrochloride and 0.15 g of 2-methoxy-4-(trifluoromethyl)benzoic acid were dissolved in 2.5 ml dimethylformamide, and 0.11 ml diethyl cyanophosphonate and 0.10 ml triethylamine were added under ice-cooling. After stirring at room temperature for 16 hours, the reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was successively washed with 1N hydrochloric acidand brine, dried over anhydrous magnesium sulfate and the solvent was evaporated.

17
[ 448-36-2 ]
[ 334015-32-6 ]
2-[4-methoxy-3-([2-methoxy-4-(trifluoromethyl)benzoyl]amino}methyl)benzyl]butanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 21e) 0.24 g of <strong>[448-36-2]2-methoxy-4-(trifluoromethyl)benzoic acid</strong> and 0.3 g of ethyl 2-[3-(aminomethyl)-4-methoxybenzyl]butanoate were treated in the same manners as in Example 19d) and then in Example 19e), to give 0.3 g of 2-[4-methoxy-3-([2-methoxy-4-(trifluoromethyl)benzoyl]amino}methyl)benzyl]butanoic acid as a pale yellow oil. 1H-NMR(CDCl3) δ: 0.93(t,J=7Hz,3H) 1.5-1.7(m,2H) 2.5-2.6(m,1H) 2.69(dd,J=7,14Hz,1H) 2.89(dd,J=8,14Hz,1H) 3.87(s,3H) 3.98(s,3H) 4.62(d,J=6Hz,2H) 6.80(d,J=8Hz,1H) 7.08(dd,J=2,8Hz,1H) 7.16(s,2H) 7.28-7.34(m,1H) 8.26-8.40(m,1H) 8.36(t,J=6Hz,1H)

References: [1]Patent: EP1216980,2002,A1 .

18
[ 334015-40-6 ]
[ 448-36-2 ]
2-isopropoxy-3-[4-methoxy-3-([2-methoxy-4-(trifluoromethyl)benzoyl]amino]methyl)phenyl]propanoicacid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 23 Example 23a) 0.15 g of ethyl 3-[3-(aminomethyl)-4-methoxyphenyl]-2-isopropoxypropanoate and 0.24 g of <strong>[448-36-2]2-methoxy-4-(trifluoromethyl)benzoic acid</strong> were treated in the same manners as in Example 19d) and then in Example 1d), to give 0.15 g of 2-isopropoxy-3-[4-methoxy-3-([2-methoxy-4-(trifluoromethyl)benzoyl]amino]methyl)phenyl]propanoicacid as a pale yellow oil. 1H-NMR(CDCl3) δ: 1.00(d,J=6Hz,3H) 1.14(d,J=6Hz,3H) 2.90(dd,J=8,14Hz,1H) 3.03(dd,J=4,14Hz,1H) 3.56(sept,J=6Hz,1H) 3.88(s,3H) 4.00(s,3H) 4.08(dd,J=4,8Hz,1H) 4.63(d,J=6Hz,2H) 6.81(d,J=8Hz,1H) 7.14(dd,J=2,8Hz,1H) 7.17(s,1H) 7.22(d,J=2Hz,1H) 7.32(d,J=8Hz,1H) 8.30(d,J=8Hz,1H) 8.35(t,J=8Hz,1H)

References: [1]Patent: EP1216980,2002,A1 .

19
[ 624-92-0 ]
[ 448-36-2 ]
[ 1208984-79-5 ]

Yield	Reaction Conditions	Operation in experiment
11%		N,N,N'N'-Tetramethylethylendiamine (21 g, 177 mmol) was added drop-wise at -70 C. to a solution of sec-butyllithium (110 mL, 1.4 M in cyclohexane, 154 mmol) in 180 mL tetrahydrofuran. 2-Methoxy-4-trifluoromethyl-benzoic acid (13 g, 59 mmol) in 60 mL tetrahydrofuran was added drop-wise at -70 C. over 2 hours. After complete addition stirring was continued at -70 C. for another 2 hours. Dimethyl disulfide (20 g, 207 mmol) was added at -70 C. within 10 min. Stirring was continued at -70 C. for another hour and the reaction was allowed to warm up. The reaction mixture was quenched with 150 mL water and extracted with 200 mL ethyl acetate. The aqueous phase was adjusted to pH1 by addition of 25% HCl and extracted twice with dichloromethane. The combined organic phases were dried on sodium sulfate, filtered and evaporated. The crude product was crystallized with heptane and yielded the title compound as a white solid (1.75 g, 11%), MS: m/e=265.1 [(M-H)-].
11%		2-Methoxy-6-methylsulfanyl-4-trifluoromethyl-benzoic acid N,N,N'N'-Tetramethylethylendiamine (21 g, 177 mmol) was added drop-wise at -70 C. to a solution of sec-butyllithium (110 mL, 1.4 M in cyclohexane, 154 mmol) in 180 mL tetrahydrofuran. 2-Methoxy-4-trifluoromethyl-benzoic acid (13 g, 59 mmol) in 60 mL tetrahydrofuran was added drop-wise at -70 C. over 2 hours. After complete addition stirring was continued at -70 C. for another 2 hours. Dimethyl disulfide (20 g, 207 mmol) was added at -70 C. within 10 min. Stirring was continued at -70 C. for another hour and the reaction was allowed to warm up. The reaction mixture was quenched with 150 mL water and extracted with 200 mL ethyl acetate. The aqueous phase was adjusted to pH1 by addition of 25% HCl and extracted twice with dichloromethane. The combined organic phases were dried on sodium sulfate, filtered and evaporated. The crude product was crystallized with heptane and yielded the title compound as a white solid (1.75 g, 11%), MS: m/e=265.1 [(M-H)-].
11%		Ν,Ν,Ν'Ν'-Tetramethylethylendiamine (21 g, 177 mmol) was added drop-wise at -70C to a solution of sec-butyllithium (110 mL, 1.4 M in cyclohexane, 154 mmol) in 180 mLtetrahydrofuran. 2-Methoxy-4-trifluoromethyl-benzoic acid (13 g, 59 mmol) in 60 mL tetrahydrofuran was added drop-wise at -70C over 2 hours. After complete addition stirring was continued at -70C for another 2 hours. Dimethyl disulfide (20 g, 207 mmol) was added at -70C within 10 min. Stirring was continued at -70C for another hour and the reaction was allowed to warm up. The reaction mixture was quenched with 150 mL water and extracted with 200 mL ethyl acetate. The aqueous phase was adjusted to pHl by addition of 25% HC1 and extracted twice with dichloromethane. The combined organic phases were dried on sodium sulfate, filtered and evaporated. The crude product was crystallized with heptane and yielded the title compound as a white solid (1.75 g, 11%), MS: m/e = 265.1 [(M-H) ].

References: [1]Patent: US2011/53904,2011,A1 .Location in patent: Page/Page column 12-13.
[2]Patent: US2011/190349,2011,A1 .Location in patent: Page/Page column 8.
[3]Patent: WO2011/95434,2011,A1 .Location in patent: Page/Page column 14-15.

20
[ 448-36-2 ]
[ 1236303-02-8 ]

Yield	Reaction Conditions	Operation in experiment
12%	With 1,2-dibromo-1,1,2,2-tetrachloroethane; N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -75 - 70℃; for 2.25h;	To -75 C. cooled THF (70 ml) was added dropwise 36 ml (50.0 mmol) of a 1.4 M sec-BuLi solution in cyclohexane within 5 minutes keeping the temperature below -70 C. 7.5 ml (50.0 mmol) TMEDA were added dropwise at temperature below -70 C. within 5 minutes. A solution of 5.0 g (22.71 mmol) <strong>[448-36-2]2-methoxy-4-(trifluoromethyl)benzoic acid</strong> (commercial) in THF (25 ml) was added dropwise at over a period of 20 minutes. The dark green solution was stirred at -75 C. for 2 hours. A solution of 29.6 g (90.84 mmol) 1,2-dibromotetrachloroethane in THF (30 ml) was added dropwise. The off-white suspension was stirred at -75 C. for 1 hour and then allowed to warm to room temperature. The yellow solution was quenched by dropwise addition of 60 ml water under ice bath cooling. The mixture was diluted with ethyl acetate (70 ml) and water (30 ml). The aqueous layer was extracted with ethyl acetate (50 ml), acidified with HCl 25% and extracted with ethyl acetate (3×50 ml). The extracts were combined, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was stirred in heptane, filtered and dried. The solid was recristallized from heptane (7 ml) and ethyl acetate (2 ml) to provide 815 mg (12%) of the title compound as a white solid. MS (m/e): 298.9 (M-H).
12%		To -75 C. cooled THF (70 ml) was added dropwise 36 ml (50.0 mmol) of a 1.4 M sec-BuLi solution in cyclohexane within 5 minutes keeping the temperature below -70 C. 7.5 ml (50.0 mmol) TMEDA were added dropwise at temperature below -70 C. within 5 minutes. A solution of 5.0 g (22.71 mmol) <strong>[448-36-2]2-methoxy-4-(trifluoromethyl)benzoic acid</strong> (commercial) in THF (25 ml) was added dropwise at over a period of 20 minutes. The dark green solution was stirred at -75 C. for 2 hours. A solution of 29.6 g (90.84 mmol) 1,2-dibromotetrachloroethane in THF (30 ml) was added dropwise. The off-white suspension was stirred at -75 C. for 1 hour and then allowed to warm to room temperature. The yellow solution was quenched by dropwise addition of 60 ml water under ice bath cooling. The mixture was diluted with ethyl acetate (70 ml) and water (30 ml). The aqueous layer was extracted with ethyl acetate (50 ml), acidified with HCl 25% and extracted with ethyl acetate (3×50 ml). The extracts were combined, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was stirred in heptane, filtered and dried. The solid was recrystallized from heptane (7 ml) and ethyl acetate (2 ml) to provide 815 mg (12%) of the title compound as a white solid. MS (m/e): 298.9 (M-H).
12%		Intermediate W: 2-Bromo-6-methoxy-4-trifluoromethyl-benzoic acidTo -75 0C cooled THF (70ml) was added dropwise 36 ml (50.0 mmol) of a 1.4 M sec-BuLi solution in cyclohexane within 5 minutes keeping the temperature below -70 0C. 7.5 ml (50.0 mmol) TMEDA were added dropwise at temperature below -70 C within 5 minutes. A solution of 5.O g (22.71 mmol) <strong>[448-36-2]2-methoxy-4-(trifluoromethyl)benzoic acid</strong> (commercial) in THF (25 ml) was added dropwise at over a period of 20 minutes. The dark green solution was stirred at -75 0C for 2 hours. A solution of 29.6 g (90.84 mmol) 1,2-dibromotetrachloroethane in THF (30ml) was added dropwise. The off-white suspension was stirred at -75 0C for 1 hour and then allowed to warm to room temperature. The yellow solution was quenched by dropwise addition of 60ml water under ice bath cooling. The mixture was diluted with ethyl acetate (70 ml) and water (30 ml). The aqueous layer was extracted with ethyl acetate (50 ml), acidified with HCl 25 % and extracted with ethyl acetate (3 x 50 ml). The extracts were combined, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was stirred in heptane, filtered and dried. The solid was recristallized from heptane (7 ml) and ethyl acetate (2 ml) to provide 815 mg (12 %) of the title compound as a white solid. MS(nVe): 298.9 (M-H).

References: [1]Patent: US2010/197715,2010,A1 .Location in patent: Page/Page column 28.
[2]Patent: US2011/53904,2011,A1 .Location in patent: Page/Page column 19.
[3]Patent: WO2011/23667,2011,A1 .Location in patent: Page/Page column 33-34.

21
[ 448-36-2 ]
C₉H₆ClF₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; N,N-dimethyl-formamide; toluene; at 0 - 80℃; for 19h;	To a solution of 24.98 g (113 mmol) 4-(trifluoromethyl)-2-methoxy-benzoic acid in 220 ml toluene were added 82 ml (1.13 mol) thionyl chloride and 5 drops dimethylformamide. The mixture was heated to 80 C. for 3 h. Then the reaction mixture was concentrated at 50 C./10 mbar. The remaining acid chloride, 27.9 g of a light yellow liquid, was dissolved in 160 ml dichloromethane, cooled to 0 C. and a solution of 20.34 g (228 mmol) 2-amino-2-methyl-propan-1-ol in 60 ml dichloromethane added. The mixture was allowed to stir at ambient temperature for 16 h. The off-white suspension was diluted with water, the aqueous phase evaporated and the organic phase extracted 3 times with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product, 33.2 g N-(2-hydroxy-1,1-dimethyl-ethyl)-2-methoxy-4-trifluoro-methyl-benzamide, a light yellow oil was dissolved in 220 ml dichloromethane and cooled to 0 C. Then 24.7 ml (340 mmol) thionyl chloride was added drop-wise and the resulting light yellow solution stirred at ambient temperature for 16 h. Then the pH was adjusted to 10 by addition of saturated aqueous Na2CO3 solution. The aqueous layer was separated and extracted 3 times with tert-butyl methyl ether. The combined organic phases were washed twice with brine, dried over Na2SO4, filtered and concentrated to provide the title compound as light yellow oil which was used without further purification. MS (m/e): 274.1 (M+H+).

References: [1]Patent: US2010/197715,2010,A1 .Location in patent: Page/Page column 33.

22
[ 448-36-2 ]
[ 1268726-07-3 ]