924312-09-4|Ethyl 2-(4-bromo-2-fluorophenyl)acetate| Ambeed

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Quality Control of [ 924312-09-4 ] Purity: 98% SDS Specification

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Product Details of [ 924312-09-4 ]

CAS No. :	924312-09-4
Formula :	C₁₀H₁₀BrFO₂
M.W :	261.09
SMILES Code :	O=C(OCC)CC1=CC=C(Br)C=C1F
MDL No. :	MFCD11046199
Boiling Point :	No data available

Safety of [ 924312-09-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 924312-09-4 ]

* 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 [ 924312-09-4 ]

[ 924312-09-4 ] Synthesis Path-Downstream 1~20

1
[ 64-17-5 ]
[ 114897-91-5 ]
[ 924312-09-4 ]

Yield	Reaction Conditions	Operation in experiment
70%		(2) Production of ethyl (4-bromo-2-fluorophenyl)acetate: Hydrochloric acid (10 mL) was added to an ethanol solution (20 mL) of (4-bromo-2-fluorophenyl)acetonitrile (2.11 g, 9.86 mmol), and heated under reflux for 15 hours. Next, with cooling with ice, aqueous saturated sodium hydrogencarbonate solution was gradually added to the reaction liquid for neutralization. After extracted with ethyl acetate, the obtained organic layer was washed with saturated saline, then dried with anhydrous sodium sulfate, and filtered. The obtained filtrate was concentrated under reduced pressure, then the residue was purified by silica gel column chromatography (hexane:ethyl acetate = 10:0 to 9:1) to obtain the entitled compound (1.81 g, 70 %). 1H-NMR (400 MHz, DMSO-d6, δ ppm): 1.26 (3H, t, J=7.2 Hz), 3.62 (2H, s), 4.17 (2H, q, J=7.2 Hz), 7.12-7.18 (1H, m), 7.23-7.28 (2H, m).

References: [1]Patent: EP1916239,2008,A1 .Location in patent: Page/Page column 33.

2
[ 19213-72-0 ]
[ 924312-09-4 ]
[ 1359827-64-7 ]

Yield	Reaction Conditions	Operation in experiment
82%		General procedure: To a stirred solution of phenyl acetic acid ethyl ester 1a (1 g, 6.09 mmol) in THF (10 mL) was added LiHMDS (9.1 ml, 1 M sol. in THF, 7.31 mmol) at -78 C and the reaction mixture was stirred at this temperature for 30 min. Ethyl-1-imidazole carboxylate 2 (1.2 g, 9.146 mmol) in dry THF (3 ml) was added drop wise to the reaction mixture at -78 C and stirred at rt for 3 h. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layer was washed with water, saturated brine solution, and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product was chromatographed on a silica gel column. Elution with 4% ethyl acetate/pet ether gave the pure compound 3a (1.1 g, 81% yield) as a colorless liquid.

References: [1]Tetrahedron Letters,2012,vol. 53,p. 1060 - 1062.

3
[ 924312-09-4 ]
[ 114897-92-6 ]

Yield	Reaction Conditions	Operation in experiment
91%		8.1/(4-bromo-2-fluorophenyl)acetic acid; 0.09 g of lithium hydroxide monohydrate is added to 0.37 g (1.4 mmol) of ethyl ester of (4-bromo-2-fluorophenyl)acetic acid in solution in 8 ml of a solvent mixture THF/methanol/water (1/1/1), and the reaction mixture is stirred for 3 h at room temperature. The reaction mixture is acidified with 1N HCl solution, then extracted with dichloromethane (20 ml). The organic phases are combined, dried over Na2SO4, filtered and concentrated under reduced pressure. 0.3 g of product is obtained in the form of gum and is used without purification in the next stage. Yield 91%.

References: [1]Patent: US2013/5724,2013,A1 .Location in patent: Page/Page column 19.

4
[ 924312-09-4 ]
2-(4-bromo-2-fluorophenyl)acetyl chloride [ No CAS ]

References: [1]Patent: US2013/5724,2013,A1 .

5
[ 924312-09-4 ]
[ 1308917-97-6 ]

References: [1]Patent: US2013/5724,2013,A1 .

6
[ 924312-09-4 ]
[ 1426050-73-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 90℃; for 9.0h;	To a stirring solution of <strong>[924312-09-4]ethyl 2-(4-bromo-2-fluorophenyl)acetate</strong> (3.92 g, 15.0 mmol) in carbon tetrachloride (50 mL) was slowly added N-bromosuccinimide (2.67 g, 15.0 mmol) and then azobisisobutyronitrile (0.37 g, 2.3 mmol). The reaction mixture was stirred for 9 h at 90 C and then cooled to room temperature. The residue was purified by flash chromatography (0-100% ethyl acetate/hexanes) to provide the title product (4.9 g, 96% yield). MS(ES)+ m/e 340.9 [M+H]+.

References: [1]Patent: WO2013/28447,2013,A1 .Location in patent: Page/Page column 113.

7
[ 924312-09-4 ]
[ 1426050-74-9 ]
[ 1426050-75-0 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of tert-butyl 4-ethyl-3-oxo-l-oxa-4,9-diazaspiro[5.5]undecane-9- carboxylate (1 g, 3.35 mmol) in dichloromethane (10 mL) was added TFA (0.775 mL, 10.05 mmol). The reaction mixture was stirred at room temperature overnight, at which point the deprotection had proceeded to completion. The reaction mixture was concentrated in vacuo, dichloromethane was added, and the solution was concentrated in vacuo again. The residue was dissolved with N,N-dimethylformamide (12 mL). To this solution was added potassium carbonate (0.463 g, 3.35 mmol) and ethyl 2-bromo-2-(4- bromophenyl)acetate (1.079 g, 3.35 mmol). The reaction mixture was stirred at 40 C for overnight, at which point the reaction had proceeded to completion. The reaction mixture was poured into water (120 mL) and was extracted with ethyl acetate (80 mL x 3). The combined organic layers were dried and concentrated in vacuo. Crude ethyl 2-(4-bromo-2- fluorophenyl)-2-(4-ethyl-3-oxo-l-oxa-4,9-diazaspiro[5.5]undecan-9-yl)acetate was obtained (590 mg) and was used directly in the next step. MS(ES)+ m/e 457 [M+H]+. To a solution of the crude ethyl 2-(4-bromo-2-fluorophenyl)-2-(4-ethyl-3-oxo-l- oxa-4,9-diazaspiro[5.5]undecan-9-yl)acetate (590 mg), 7-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)quinoline (329 mg, 1.29 mmol) and 2M aq K2CO3 (1.4 mL, 2.8 mmol) in 1,4-dioxane (2.5 mL) was added PdCl2(dppf)-CH2Cl2 adduct (53 mg, 0.065 mmol). The reaction mixture was purged with nitrogen, sealed, and irradiated in the microwave at 110 C for 25 min, at which point the reaction had proceeded to completion. The reaction mixture was diluted with ethyl acetate (25 mL) and washed with 5 mL of 1M aq HC1. The organic phase was washed with brine (5 mL), dried over anhydous sodium sulfate, filtered through a pad of celite, and concentrated in vacuo. The crude product was purified with reverse phase HPLC (25-55% acetonitrile + 0.1 %TFA:water + 0.1 % TFA). The appropriate fractions were collected and evaporated to yield the title compound as a trifiuoroacetate salt (31 mg, 2% over the two steps). MS(ES)+ m/e 506 [M+H]+; 1H NMR (400 MHz, CD2C12) δ ppm 1.14 (t, J=7.20 Hz, 3 H) 1.28 (t, J=7.07 Hz, 3 H) 2.14 (s, 1 H) 2.11 (s, 1 H) 2.28 - 2.38 (m, 2 H) 3.05 (t, J=l 1.75 Hz, 1 H) 3.22 (t, J=13.26 Hz, 1 H) 3.30 (s, 2 H) 3.44 (d, J=7.07 Hz, 2 H) 3.62 (d, J=10.11 Hz, 1 H) 3.76 (d, J=13.89 Hz, 1 H) 4.06 (s, 2 H) 4.29 - 4.41 (m, 2 H) 5.43 (s, 1 H) 7.71 - 7.82 (m, 3 H) 7.89 - 7.96 (m, 1 H) 8.13 (d, J=8.59 Hz, 1 H) 8.26 (d, J=8.59 Hz, 1 H) 8.79 - 8.84 (m, 2 H) 9.27 - 9.32 (m, 1 H).

References: [1]Patent: WO2013/28447,2013,A1 .Location in patent: Page/Page column 113-114.

8
[ 114897-92-6 ]
[ 64-17-5 ]
[ 924312-09-4 ]

Yield	Reaction Conditions	Operation in experiment
87.5%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	(Intermediate 2) 5-(4-Cyclopropyl-2-fluorophenyl)-4-oxo-1-(tetrahydro-2H-pyran-4-ylmethyl)-1,4-dihydropyridine-3-carboxylic acid (Step 1) Ethyl (4-bromo-2-fluorophenyl)acetate To a solution of (4-bromo-2-fluorophenyl)acetic acid (2.00 g, 8.58 mmol) in methylene chloride (40.0 mL), ethanol (0.969 mL, 0.791 g, 17.2 mmol), 4-dimethylaminopyridine (0.105 g, 0.858 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDAC.HCl) (1.97 g, 10.3 mmol) were added, and the mixture was stirred overnight at room temperature. To the reaction mixture, 1 N hydrochloric acid was added, followed by extraction with methylene chloride three times. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and brine in this order and then dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the residue obtained was purified by silica gel column chromatography (Yamazen Corp., n-hexane/ethyl acetate=(100/0->87/13) to obtain the title compound (1.96 g, yield: 87.5%) as a solid. 1H-NMR (CDCl3) δ: 7.27-7.24 (2H, m), 7.18-7.14 (1H, m), 4.17 (2H, q, J=7.0 Hz), 3.62 (2H, s), 1.26 (3H, t, J=7.0 Hz).

References: [1]Patent: US2017/183329,2017,A1 .Location in patent: Paragraph 0371-0373.

9
[ 924312-09-4 ]
(4-cyclopropyl-2-fluorophenyl)acetic acid [ No CAS ]

References: [1]Patent: US2017/183329,2017,A1 .

10
[ 924312-09-4 ]
[ 411235-57-9 ]
ethyl (4-cyclopropyl-2-fluorophenyl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95.8%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃; for 2.0h;Inert atmosphere;	(Step 2) Ethyl (4-cyclopropyl-2-fluorophenyl)acetate To a suspension of ethyl (4-bromo-2-fluorophenyl)acetate (1.95 g, 7.47 mmol) synthesized in step 1 in toluene (30.0 mL), cyclopropylboronic acid (0.962 g, 11.2 mmol), tricyclohexylphosphine (0.419 g, 1.49 mmol), tripotassium phosphate (5.55 g, 26.1 mmol), and water (6.00 mL) were added, and the reaction mixture was purged with nitrogen. Then, palladium(II) acetate (0.168 g, 0.747 mmol) was added, and the mixture was stirred at 100 C. for 2 hours. The reaction mixture was left to cool to room temperature, and then, water was added thereto, followed by extraction with ethyl acetate three times. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the obtained residue was purified by silica gel column chromatography (Yamazen Corp., n-hexane/ethyl acetate=100/0->87/13) and further purified by amino silica gel column chromatography (Yamazen Corp., n-hexane/ethyl acetate=100/0->87/13) to obtain the title compound (1.59 g, yield: 95.8%) as an oil. 1H-NMR (CDCl3) δ: 7.12 (1H, t, J=7.9 Hz), 6.84-6.82 (1H, m), 6.76-6.72 (1H, m), 4.16 (2H, q, J=7.0 Hz), 3.61 (2H, s), 1.90-1.83 (1H, m), 1.25 (3H, t, J=7.0 Hz), 1.00-0.95 (2H, m), 0.70-0.66 (2H, m). MS (APCI) m/z: 223 [(M+H)+].

References: [1]Patent: US2017/183329,2017,A1 .Location in patent: Paragraph 0374-0376.

11
[ 924312-09-4 ]
[ 73183-34-3 ]
ethyl 2-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃; for 3.0h;Inert atmosphere;	Ethyl 2-(4-bromo-2-fluorophenyl)acetate (2.7g, 10.3mmol),Pinacol diboronic acid ester (3.15g, 12.4mmol),Pd(dppf)Cl2 (0.23g, 0.3mmol) andPotassium acetate (3.04g, 31mmol)Add to 50mL dioxane,It was replaced with nitrogen three times, and the temperature was raised to 90C to react for 3 hours.The reaction solution was cooled to room temperature, 100 mL of water was added, and it was extracted with ethyl acetate (50 mL*3). The organic phase was washed with 40 mL of saturated brine, dried over anhydrous sodium sulfate, and concentrated.2.21 g of light yellow solid was obtained through silica gel column separation, with a yield of 70%.

References: [1]Patent: CN112552302,2021,A .Location in patent: Paragraph 0561-0566.

12
[ 924312-09-4 ]
2-(4-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-fluorophenyl)ethanoic acid ethyl ester [ No CAS ]

References: [1]Patent: CN112552302,2021,A .

13
[ 924312-09-4 ]
2-(4-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-fluorophenyl)ethanoic acid [ No CAS ]

References: [1]Patent: CN112552302,2021,A .

14
[ 924312-09-4 ]
2-(4-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-fluorophenyl)-N-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)acetamide [ No CAS ]

References: [1]Patent: CN112552302,2021,A .

15
[ 924312-09-4 ]
tert-butyl 4-[4-(2-ethoxy-2-oxoethyl)-3-fluorophenyl]piperidine-1-carboxylate [ No CAS ]