60312-83-6|2-(3-Bromophenyl)acetamide| Ambeed

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Quality Control of [ 60312-83-6 ] Purity: 96% SDS Specification

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Product Details of [ 60312-83-6 ]

CAS No. :	60312-83-6
Formula :	C₈H₈BrNO
M.W :	214.06
SMILES Code :	O=C(N)CC1=CC=CC(Br)=C1
MDL No. :	MFCD07781225
InChI Key :	JEYSSRJRKIAJIO-UHFFFAOYSA-N
Pubchem ID :	11736027

Safety of [ 60312-83-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 60312-83-6 ]

* 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 [ 60312-83-6 ]

[ 60312-83-6 ] Synthesis Path-Downstream 1~22

1
[ 110-91-8 ]
[ 60312-83-6 ]
[ 103-81-1 ]
2-(3-Morpholin-4-yl-phenyl)-acetamide [ No CAS ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 7181 - 7184.

2
2-[(3-bromo-phenyl)-acetylimino]-2-(4-methoxy-phenyl)-<i>N</i>,<i>N</i>-dimethyl-acetamide [ No CAS ]
[ 60312-83-6 ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 6926 - 6927.

3
[ 5720-06-9 ]
[ 60312-83-6 ]
[ 663926-13-4 ]

Yield	Reaction Conditions	Operation in experiment
		[2- (3-BROMO-PHENYL)-ACETAMIDE] (1.07 g, 5.00 mmol) is dissolved in THF (30 ml) and cooled to [0C.] 2-methoxyphenylboronic acid (0.76 g, 5.00 mmol) is added then sodium carbonate (1.06 g, 10.00 mmol) dissolved in water (24 ml). The reaction mixture is evacuated and charged with argon (3x). Tetrakis (triphenylphosphine) palladium (0.29 g, 0.25 mmol) is added and the reaction mixture is evacuated and charged with argon (3x). The reaction mixture is stirred at [800 C] for 18 hours. The reaction mixture is extracted with ethyl acetate and the organic layer is washed with water (150 [ML)] and brine (150 ml), dried over [MGSO4,] filtered and the solvent removed in vacuo. The title compound is obtained after purification by flash column chromatography (silica, ethyl acetate). MS (ES+) m/e 242 (MH+).

References: [1]Patent: WO2004/16601,2004,A1 .Location in patent: Page 32.

4
[ 60312-83-6 ]
[ 73183-34-3 ]
[ 843646-72-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; 1,1'-bis(diphenylphosphino)ferrocene; In 1,4-dioxane; at 90℃; for 18h;Inert atmosphere;	In a Schlenk tube, a mixture of <strong>[60312-83-6]2-(3-bromophenyl)acetamide</strong> (1.0 g, 4.67 mmol), bis(pinacolato)diboron (2.37 g, 9.34 mmol) and potassium acetate (1.38 g, 14 mmol) was dissolved in dioxane (40ml). The mixture was purged (vacuum-argon three times) and [1,1-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)dichloromethane complex (0.19 g, 0.23 mmol) and 1,1'-bis(diphenylphospheno)ferrocene (0.13 g, 0.23 mmol) were added. The mixture was purged again (vacuum-argon three times) and stirred at 90 C for 18 h. The suspension was filtered off and the filtrated diluted with water and extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, and dried over anhydrous sodium sulphate. Solvent was removed in vacuum and the residue was purified by the SP1 automated purification system to give 0.95 g (3.64 mmol) of the desired compound. Yield = 78% HPLC/MS (15 min) retention time 6.28 min. LRMS: m/z 262 (M+1)
65%	With potassium acetate;palladium diacetate; In DMF (N,N-dimethyl-formamide); at 80℃; for 12.3333h;	A mixture of 2- (3-BROMO-PHENYL)-ACETAMIDE (600 mg, 2.8 MMOL), potassium acetate (63 mg, 0.28 mmol, 0.1 eq), bis (pinacolato) diboron (783 mg, 3.08 mmol, 1.1 eq), in anhydrous DMF was degassed under N2 for 10 min. Then palladium acetate (824 mg, 8.41 mmol, 3 eq) was added, and the mixture degassed an additional 10 min. The reaction was then heated to 80 C for 12 h. The reaction mixture was then poured into ethyl acetate and water. Extracted with ethyl acetate (3 x 20 mL). The combined organic layer was dried with sodium sulfate, filtered through celite pad and concentrated in vacuo. The crude material was used directly to the next step. Yield : (473 mg, 65%). LC-MS (MH+ = 262).

References: [1]Patent: EP2196465,2010,A1 .Location in patent: Page/Page column 30.
[2]Patent: WO2005/14566,2005,A1 .Location in patent: Page/Page column 96-97.

5
[ 31938-07-5 ]
[ 60312-83-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium percarbonate; In water; acetone; at 60℃;	A solution of 3-bromophenylacetonitrile (1.0 g, 5.10 MMOL) in acetone (25 mL) and water (15 mL) was treated with sodium percarbonate. The reaction was stirred at 60 C overnight. The organic solvent was removed at reduced pressure and the residue was diluted with ethyl acetate and water. The layers were separated and the organic was washed with brine and dried over magnesium sulfate. The solvent was removed at reduced pressure and the residue was washed with diethyl ether-hexanes (1/1, v/v) to afford 0.65 g of product (60%) as a white SOLID. RF= 0.18 (silica, ethyl acetate: hexanes, 3: 2) ;'H-NMR (DMSO-d6) 8 7.50 (bs, 1H), 7.46 to 7.39 (m, 2H), 7.26 to 7.22 (m, 2H), 6.93 (BS, 1 H), 3.37 (s, 2H).
60%	With sodium percarbonate; In water; acetone; at 60℃;	Example 21; Method H-14; Preparation of 2-(3-bromo->henvl)-acetamide; A solution of 3-bromophenylacetonitrile (1.0 g, 5.10 mmol) in acetone (25 mL) and water (15 mL) was treated with sodium percarbonate. The reaction was stirred at 60 C overnight. The organic solvent was removed at reduced pressure and the residue was diluted with ethyl acetate and water. The layers were separated and the organic was washed with brine and dried over magnesium sulfate. The solvent was removed at reduced pressure and the residue was washed with diethyl ether-hexanes (1/1, v/v) to afford 0.65 g of product (60%) as a white solid. Rf= 0.18 (silica, ethyl acetate: hexanes, 3: 2) ; 1H-NMR (DMSO-d6) 6 7.50 (bs, 1 H), 7.46 to 7.39 (m, 2H), 7.26 to 7.22 (m, 2H), 6.93 (bs, 1H), 3.37 (s, 2H).
60%	With sodium percarbonate; In water; acetone; at 60℃;	Preparation of 2-(3-bromo-phenyl)-acetamide. A solution of 3-bromophenylacetonitrile (1.0 g, 5.10 mmol) in acetone (25 mL) and water (15 mL) was treated with sodium percarbonate. The reaction was stirred at 60 0C overnight. The organic solvent was removed at reduced pressure and the residue was diluted with ethyl acetate and water. The layers were separated and the organic was washed with brine and dried over magnesium sulfate. The solvent was removed at reduced pressure and the residue was washed with diethyl ether - hexanes (1/1, v/v) to afford 0.65 g of product (60%) as a white solid. Rf = 0.18 (silica, ethyl acetate:hexanes, 3:2); 1H-NMR (DMSO-d6) 7.50 (bs, IH), 7.46 to 7.39 (m, 2H), 7.26 to 7.22 (m, 2H), 6.93 (bs, IH), 3.37 (s, 2H).

References: [1]ACS Catalysis,2021,vol. 11,p. 10239 - 10245.
[2]Patent: WO2005/14566,2005,A1 .Location in patent: Page/Page column 96.
[3]Patent: WO2003/72561,2003,A1 .Location in patent: Page/Page column 26-27.
[4]Patent: WO2008/25509,2008,A1 .Location in patent: Page/Page column 49-50.

6
[ 1878-67-7 ]
[ 60312-83-6 ]

Yield	Reaction Conditions	Operation in experiment
75.4%	With ammonium chloride; N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 4h;	To a stirred solution of compound 0419-1 (2.0 g, 9.3 mmol) in DMF (25 ml) was added (2173) NH4CI (497 mg, 9.3 mmol), HATU (5.3 g, 13.95 mmol), and DIEA (3.6 g, 27.9 mmol) was stirred at rt for 4 h. Then added water, the aqueous phase was extracted with dichloromethane, the combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo , purified by C.C. to give 419-2 (1.5 g, yield: 75.4%) as a white solid.
		Example 1 Synthesis of 2-(3-bromophenyl)acetamide 1-Hydroxybenzotriazole (HOBT, 13.82 g, 102.3 mmol), N-ethyldiisopropyl amine (Hunig's base, 13.22 g, 102.3 mmol) and ammonium carbonate (27.0 g, 279.0 mmol) were added to a solution of (3-bromophenyl)acetic acid (20.0 g, 93.0 mmol) in freshly dried and distilled tetrahydrofuran (80 mL) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for about 5 minutes and then cooled to 0 C and stirred at the same temperature for about 1 hour. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI.HCl, 19.61 g, 102.3 mmol) was added at 0 C under nitrogen atmosphere. The reaction mixture was stirred at room temperature for about 12 hours. The solvent was evaporated under vacuum and water was added. A white solid was obtained which was filtered, washed with water and dried. Yield: 12.69 g. 1H NMR (400 MHz, DMSO-d6): δ 7.52 (brs, 1H, -NH), 7.46 (s, 1H, Ar-H), 7.43-7.40 (m, 2H, Ar-H), 7.25-7.18 (m, 2H, Ar-H), 6.95 (brs, 1H, -NH) and 3.34 (s, 2H, -CH2). Mass Spectrum (m/z, +ve ion mode): 214 [M++1]
		1-Hydroxybenzotriazole (HOBT, 13.82 g, 102.3 mmol), N-ethyldiisopropyl amine (Hunig's base, 13.22 g, 102.3 mmol) and ammonium carbonate (27.0 g, 279.0 mmol) were added to a solution of (3-bromophenyl)acetic acid (20.0 g, 93.0 mmol) in freshly dried and distilled tetrahydrofuran (80 ml) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for about 5 min and then cooled to 0 C. and stirred at the same temperature for about 1 hour. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI.HCl, 19.61 g, 102.3 mmol) was added to it at 0 C. under nitrogen atmosphere. The reaction mixture was stirred at room temperature for about 12 hours. The solvent was evaporated under vacuum and water was added to it. A white solid was obtained which was filtered, washed with water and dried. Yield: 12.69 g. 1H NMR (400 MHz, DMSO-d6): δ 7.52 (brs, 1H, -NH), 7.46 (s, 1H, Ar-H), 7.43-7.40 (m, 2H, Ar-H), 7.25-7.18 (m, 2H, Ar-H), 6.95 (brs, 1H, -NH) and 3.34 (s, 2H, -CH2). Mass Spectrum (m/z, +ve ion mode): 214 [M++1]

References: [1]Patent: WO2021/155004,2021,A1 .Location in patent: Paragraph 1561-1563.
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2390 - 2394.
[3]Patent: EP1834953,2007,A1 .Location in patent: Page/Page column 20.
[4]Patent: US2008/21080,2008,A1 .Location in patent: Page/Page column 17.
[5]Patent: WO2004/16601,2004,A1 .
[6]Bioorganic and Medicinal Chemistry Letters,2021,vol. 37.

7
[ 60312-83-6 ]
[ 31938-07-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; trifluoroacetic anhydride; In 1,4-dioxane; at 0 - 20℃; for 12h;	Example 2 Synthesis of (3-bromophenyl)acetonitrile 2-(3-Bromophenyl)acetamide (10.0 g, 46.73 mmol) (example 1) in dry 1,4-dioxane (100 mL) was cooled to 0 C. Triethylamine (18.91 g, 187.92 mmol) was added and the reaction mixture was stirred for about 10 minutes. Trifluoroacetic anhydride (39.26 g, 186.92 mmol) was added dropwise at 0 C and the reaction mixture was stirred at room temperature for about 12 hours. The reaction mixture was poured into cold water, extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulphate, filtered and the solvent evaporated under vacuum. An oily residue was obtained which was purified by column chromatography over silica gel using ethyl acetate and hexane (1:49) to afford the title compound as light yellow colored oil. Yield: 8.4 g. 1H NMR (300 MHz, CDCl3): δ 7.49-7.46 (m, 2H, Ar-H), 7.27-7.23 (m, 2H, Ar-H) and 3.73 (s, 2H, -CH2CN). Mass Spectrum (m/z, +ve ion mode): 197 [M++1]
	With triethylamine; trifluoroacetic anhydride; In 1,4-dioxane; at 0 - 20℃; for 12h;	2-(3-Bromophenyl)acetamide (10.0 g, 46.73 mmol) (example 1) in dry 1,4-dioxane (100 ml) was cooled to 0 C. Triethylamine (18.91 g, 187.92 mmol) was added to it and the reaction mixture was stirred for about 10 minutes. Trifluoroacetic anhydride (39.26 g, 186.92 mmol) was added dropwise to this solution at 0 C. and then the reaction mixture was stirred at room temperature for about 12 hours. It was poured into cold water, extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulphate, filtered and the solvent evaporated under vacuum. An oily residue was obtained which was purified by column chromatography over silica gel using ethyl acetate and hexane (1:49) to afford the title compound as light yellow colored oil. Yield: 8.4 g. 1H NMR (300 MHz, CDCl3): δ 7.49-7.46 (m, 2H, Ar-H), 7.27-7.23 (m, 2H, Ar-H) and 3.73 (s, 2H, -CH2CN). Mass Spectrum (m/z, +ve ion mode): 197 [M++1]

References: [1]Patent: EP1834953,2007,A1 .Location in patent: Page/Page column 20.
[2]Patent: US2008/21080,2008,A1 .Location in patent: Page/Page column 17-18.

8
[ 1024583-82-1 ]
[ 60312-83-6 ]
[ 1024584-25-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2390 - 2394.

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide; potassium carbonate; In dimethyl sulfoxide; at 0 - 20℃; for 72h;	General procedure: To a slurry of 3-bromo-2-methoxybenzamide (0.933 g; 4.40 mmol) and K2CO3(0.304 g; 2.2 mmol) in DMSO (10 mL) at 0 C. was added H2O2(0.5 mL of a 30 wt % solution; 4.8 mmol), dropwise over 2 min. The cooling bath was removed, the mixture was stirred at room temperature 3 days, poured into water and precipitated solid was collected by filtration. The filtrate was extracted 3×EtOAc, combined organics were washed (water, brine), dried over Na2SO4and concentrated in vacuo. The residue was combined with the above precipitated solid and the whole was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless solid.

10
[ 60312-83-6 ]
6-bromo-4-[cyclohexyl(methyl)amino]-1,1-dimethyl-1,4-dihydroisoquinolin-3(2H)-one [ No CAS ]

References: [1]Patent: US2017/233402,2017,A1 .

11
[ 60312-83-6 ]
4,6-dibromo-1,1-dimethyl-1,4-dihydroisoquinolin-3(2H)-one [ No CAS ]

References: [1]Patent: US2017/233402,2017,A1 .

12
[ 67-64-1 ]
[ 60312-83-6 ]
6-bromo-1,1-dimethyl-1,4-dihydroisoquinolin-3(2H)-one [ No CAS ]
8-bromo-1,1-dimethyl-1,4-dihydroisoquinolin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.01 g; 996 mg	With phosphorus pentoxide; phosphoric acid; at 80 - 140℃; for 4h;	To a solid of P2O5 (50.0 g) was added 34 H3PO4 (50.6 g), and the mixture was stirred at 140 C. for 1.5 hours. To the mixture were added 35 <strong>[60312-83-6]2-(3-bromophenyl)acetamide</strong> (5.00 g) and 36 acetone (3.5 mL) at 80 C., and then stirred at 140 C. for 2 hours. To the mixture was added acetone (2.0 mL) at 140 C., and stirred at the same temperature for 1 hour. And then, to the mixture was added acetone (2.0 mL) at 140 C. again, and stirred at the same temperature for additional 1 hour. The mixture was poured into iced water, and diluted with EtOAc, and the phases were separated. The organic layer was washed with sat. aq. NaHCO3 and brine, and dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3/MeOH). The obtained solid was washed with 50% EtOAc/hexanes to give 37 6-bromo-1,1-dimethyl-1,4-dihydroisoquinolin-3(2H)-one (2.01 g) as a solid. The mother liquid was concentrated under reduced pressure to give the 1:1 mixture of 6-bromo-1,1-dimethyl-1,4-dihydroisoquinolin-3(2H)-one and 8-bromo-1,1-dimethyl-1,4-dihydroisoquinolin-3(2H)-one (996 mg) as a solid.

References: [1]Patent: US2017/233402,2017,A1 .Location in patent: Paragraph 0606.

13
[ 150529-73-0 ]
[ 60312-83-6 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; In methanol; at 20℃; for 18h;	(3-Bromo-phenyl) -acetic acid methyl ester (15.33 g, 66.90 mmol) is dissolved in methanol [(50] ml) and ammonium hydroxide (100 ml). The reaction mixture is stirred at room temperature. The reaction is shown to be complete by TLC after 18 hours. The methanol is removed in vacuo and the product precipitates out. The solid is filtered off, washed with water and dried to give the title compd. MS (ES+) [MLE] 214 [(MH+-BR79),] 216 [(MH+-BR8L).]

References: [1]Patent: WO2004/16601,2004,A1 .Location in patent: Page 32.

14
[ 111409-79-1 ]
[ 60312-83-6 ]
2-(5-bromo-2-((triisopropylsilyl)ethynyl)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) acetate; sodium acetate; silver(I) triflimide; In 1,2-dichloro-ethane; at 120℃; under 760.051 Torr; for 12h;Schlenk technique; Inert atmosphere;	1 g (42.4 mg, 0.20 mmol) of a phenylacetamide compound and a trivalent ruthenium catalyst [Cp*IrCl2] 2 (1.60 mg, 0.002 mmol) were sequentially added to a 15 mL Schlenk reaction tube under an atmosphere of atmospheric pressure.Bis-trifluoromethanesulfonimide silver salt (3.9 mg, 0.01 mmol), sodium acetate (2.5 mg, 0.03 mmol), silver acetate (10.0 mg, 0.06 mmol),Finally, a solution of the alkynyl compound 2a (20 μL, 0.30 mmol) in 1,2-dichloroethane (DCE, 1 mL) was charged into the reactor with a syringe and reacted at a temperature of 120 C for 12 h.After completion of the reaction, the mixture was cooled to room temperature, suction filtered over Celite, and evaporated.The crude product was chromatographed on the prepared silica gel plate, and the selected developing solvent or eluent was petroleum ether and ethyl acetate in a volume ratio of 10:1.The product 2-(5-bromo-2-((triisopropyl)ethynyl)phenyl)acetamide (3 g) was obtained, 51.1 mg, yield 65%, purity 95%.

References: [1]Patent: CN109942616,2019,A .Location in patent: Paragraph 0113-0118.
[2]Chinese Journal of Chemistry,2020,vol. 38,p. 929 - 934.

15
[ 98288-51-8 ]
[ 60312-83-6 ]