337529-74-5|Methyl 2-Fluoro-4-nitrophenylacetate| Ambeed

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Quality Control of [ 337529-74-5 ] Purity: 98% SDS Specification

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Product Details of [ 337529-74-5 ]

CAS No. :	337529-74-5
Formula :	C₉H₈FNO₄
M.W :	213.16
SMILES Code :	O=C(OC)CC1=CC=C([N+]([O-])=O)C=C1F
MDL No. :	MFCD12198847
InChI Key :	ZFELCQQSVRXXGP-UHFFFAOYSA-N
Pubchem ID :	18369150

Safety of [ 337529-74-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 337529-74-5 ]

* 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 [ 337529-74-5 ]

[ 337529-74-5 ] Synthesis Path-Downstream 1~24

1
[ 337529-74-5 ]
[ 869335-22-8 ]
[ 869335-30-8 ]

References: [1]Patent: WO2005/108397,2005,A1 .Location in patent: Page/Page column 38-39.
[2]Tetrahedron Letters,2006,vol. 47,p. 2069 - 2072.

2
[ 337529-74-5 ]
[ 133777-96-5 ]
methyl α-[2-[[bis[(4-methoxyphenyl)methyl]amino] sulfonyl]ethyl]-2-fluoro-4-nitrobenzeneacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate;18-crown-6 ether; In toluene; for 3h;Heating / reflux;	Step 1 Preparation of methyl alpha-[2-[[bis[(4-methoxyphenyl)methyl]amino] sulfonyl]ethyl]-2-fluoro-4-nitrobenzeneacetate Methyl 2-(2-fluoro-4-nitrophenyl)acetate (25.0 g, 117.4 mmol), vinyl sulfonamide (35.0 g, 100.9 mmol), anhydrous potassium carbonate (10.0 g, 72.5 mmol) and 18-crown-6 (2.64 g, 10.0 mmol) are heated under reflux in toluene (250 ml) for 3 hr. After cooling, ethyl acetate (500 ml) and water (300 ml) are added. The organic layer is washed with brine (200 ml), dried over MgSO4, filtered and evaporated. The resultant oil is chromatographed over silica gel (1 kg) eluting with 25-50% ethyl acetate-hexane. The title compound is obtained as white crystals (45.8 g, 81%) mp 79.

References: [1]Patent: US6348459,2002,B1 .Location in patent: Page column 9.

3
[ 337529-74-5 ]
[ 1562-34-1 ]
C₁₇H₁₆FNO₇S [ No CAS ]

References: [1]Patent: US6348459,2002,B1 .Location in patent: Page column 7.

4
[ 337529-74-5 ]
[ 53412-78-5 ]
C₁₀H₁₁FN₂O₆S [ No CAS ]

References: [1]Patent: US6348459,2002,B1 .Location in patent: Page column 9.

5
[ 188975-47-5 ]
[ 337529-74-5 ]

Yield	Reaction Conditions	Operation in experiment
64%	With water; sodium chloride; In dimethyl sulfoxide; at 120℃; for 3h;	Step 2: To a stirred solution of dimethyl 2-(2-fluoro-4-nitrophenyl)malonate (5.0 g, 18.5 mmol, 1 .0 eq) in DMSO (30 mL) was added NaCl (1 .07 g, 18.5 mmol, 1 .0 eq) and water (0.5 mL) and stirred at 120 C for 3 h. The reaction mixture was diluted with water (100 mL) , extracted with EtOAc (50 mL x 2), washed with brine, dried over Na2SO4 and the solvent evaporated. The crude residue was purified by CC using PE/EtOAc (19:1 ) to get methyl 2-(2-fluoro-4-nitrophenyl)acetate (2.5g, 64%) as a viscous oil (TLC system: EtOAc/PE (1 :4), Rf: 0.55).

References: [1]Patent: WO2013/68461,2013,A1 .Location in patent: Page/Page column 133.
[2]Patent: WO2005/108397,2005,A1 .Location in patent: Page/Page column 37-38.

6
[ 369-34-6 ]
[ 337529-74-5 ]

References: [1]Patent: WO2013/68461,2013,A1 .

7
[ 337529-74-5 ]
[ 1402581-57-0 ]

References: [1]Patent: WO2013/68461,2013,A1 .

8
[ 337529-74-5 ]
[ 1402581-59-2 ]

References: [1]Patent: WO2013/68461,2013,A1 .

9
[ 337529-74-5 ]
[ 1402586-84-8 ]

References: [1]Patent: WO2013/68461,2013,A1 .

10
[ 337529-74-5 ]
[ 1221119-68-1 ]

Yield	Reaction Conditions	Operation in experiment
77%	With methanol; sodium tetrahydroborate; at 0 - 70℃; for 16h;	Step 3: To a stirred solution of <strong>[337529-74-5]methyl 2-(2-fluoro-4-nitrophenyl)acetate</strong> (3.0g, 14.0 mmol, 1 .0 eq) in methanol (30 mL) was added NaBH4 (2.08g, 36.3mmol, 4.0eg) at 0C and stirred at 70 C for 16h, then the methanol was evaporated and the residue was diluted with water (30 mL), the pH adjusted to being neutral with 2N HCI and the mixture extracted with EtOAc (50 mL x 3). The organic layer was separated, washed with brine, dried over Na2S04 and the solvent evaporated to yield 2-(2-fluoro-4-nitrophenyl)ethanol (2.0 g, 77%) as a viscous oil (TLC system: EtOAc/PE (3:7), Rf: 0.3).

References: [1]Patent: WO2013/68461,2013,A1 .Location in patent: Page/Page column 133; 134.

11
[ 337529-74-5 ]
2-(4-amino-2-fluorophenyl)ethanol [ No CAS ]

References: [1]Patent: WO2013/68461,2013,A1 .

12
[ 337529-74-5 ]
[ 74-88-4 ]
methyl 2-(2-fluoro-4-nitrophenyl)-2-methylpropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0℃; for 4h;	To a solution of <strong>[337529-74-5]methyl 2-(2-fluoro-4-nitrophenyl)acetate</strong> (10.7 g, 50.20 mmol) and iodomethane (12.55 mL, 200.79 mmol) in DMF (100 mL) was added sodium hydride (60% oil, 5.02 g, 125.49 mmol) at 0C, and the mixture was stirred at 0C for 4 hr. To the reaction mixture was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5?20% ethyl acetate/hexane) to give methyl 2-(2-fluoro-4-nitrophenyl)-2-methylpropanoate (12.10 g, 50.2 mmol, 100%) as a yellow solid.

References: [1]Patent: TW2016/2105,2016,A .Location in patent: Paragraph 0712.

13
[ 67-56-1 ]
[ 315228-19-4 ]
[ 337529-74-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sulfuric acid; for 4h;Reflux;	A solution of conc. sulfuric acid (1 mL, 18.76 mmol) and 2-(2-fluoro-4-nitrophenyl)acetic acid (10 g, 50.22 mmol) in MeOH (200 mL) was heated under reflux for 4 hr. To the reaction mixture was added aqueous sodium hydrogen carbonate solution until the mixture became neutral, and the mixture was concentrated under reduced pressure. To the residue were added ethyl acetate and water, and the organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give methyl 2-(2-fluoro-4-nitrophenyl)acetate (10.70 g, 50.2 mmol, 100%) as a pale yellow solid.
88%	With sulfuric acid;Reflux;	2-(2-fluoro-4-nitrophenyl)acetic acid (4.0 g, 0.02 mol) in methanol (20 ml) was added concentrated sulfuric acid (1 ml). The solution was heated to reflux overnight. After cooling, the mixture was concentrated to a small amount and partitioned between ether (30 ml) and water. The ether phase was separated and washed with saturated sodium bicarbonate solution (30 ml). The organic phase was then separated again and washed with water, dried over MgSO4. The solid was filtered off and evaporation of the solvent to give the product pure enough for the next step (3.8 g, 88%), MS (+) ES: 214 (M+H)+.
38%	With thionyl chloride; at 20℃;	In a 50 mL round-bottomed flask 2-fluoro-4-nitrobenzene acetic acid (800 mg, 4.0 mmol) was dissolved in MeOH (10 mL). Catalytic thionyl chloride was added and the solution stirred at room temperature overnight. The solvent was evaporated, and the residue purified using column chromatography (pentane/Et20, 9/1 to 5/1 ) to afford the title compound T-20 (325 mg, 38%) as a colorless oil.

References: [1]Patent: TW2016/2105,2016,A .Location in patent: Paragraph 0711.
[2]Patent: WO2019/213470,2019,A1 .Location in patent: Page/Page column 97; 98.
[3]Patent: WO2018/107289,2018,A1 .Location in patent: Page/Page column 23.

14
[ 337529-74-5 ]
[ 192650-54-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	With palladium on activated charcoal; hydrogen; In ethyl acetate; for 5h;	To a 50 ml round bottom flask, were added <strong>[337529-74-5]methyl 2-(2-fluoro-4-nitrophenyl)acetate</strong> (3.8 g, 0.018 mol) and ethyl acetate (30 ml). To the same flask, 10 percent palladium on activated carbon (0.5 g) was added. The reaction mixture was stirred under hydrogen gas (using bladder) atmosphere for 5 h. The reaction mixture was filtered through a pad of celite. The filtrate was evaporated under reduced pressure to get the title compound (2.8 g, 86%), MS (+) ES: 184 (M+H)+.
	With palladium 10% on activated carbon; hydrogen; In methanol;	In a 50 mL round-bottomed flask 20 (300 mg, 1.4 mmol) was dissolved in MeOH (10 mL) and Pd/C (10%, 75 mg) was added and the mixture hydrogenated with a hydrogen balloon overnight. The mixture was filtered, and evaporated to afford the title compound T-21 quantatively as a reddish oil which was used without further purification.

References: [1]Patent: WO2019/213470,2019,A1 .Location in patent: Page/Page column 97; 98.
[2]Patent: WO2018/107289,2018,A1 .Location in patent: Page/Page column 23.

15
[ 337529-74-5 ]
C₂₃H₂₈FNO₄S [ No CAS ]

References: [1]Patent: WO2018/107289,2018,A1 .

16
[ 337529-74-5 ]
C₂₂H₂₆FNO₄S [ No CAS ]

References: [1]Patent: WO2018/107289,2018,A1 .

17
[ 337529-74-5 ]
2-(4-((ethoxycarbonothioyl)thio)-2-fluorophenyl)acetic acid methyl ester [ No CAS ]