39489-67-3|2-(4-Bromophenoxy)acetonitrile| Ambeed

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Quality Control of [ 39489-67-3 ] Purity: 98% SDS Specification

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Product Details of [ 39489-67-3 ]

CAS No. :	39489-67-3
Formula :	C₈H₆BrNO
M.W :	212.04
SMILES Code :	N#CCOC1=CC=C(Br)C=C1
MDL No. :	MFCD00464958
InChI Key :	PMDDXFGYBKIPKR-UHFFFAOYSA-N
Pubchem ID :	598823

Safety of [ 39489-67-3 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302+H312-H315-H319-H331-H335
Precautionary Statements:	P261-P280-P305+P351+P338-P311
Class:	6.1
UN#:	3439
Packing Group:	Ⅲ

Application In Synthesis of [ 39489-67-3 ]

* 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 [ 39489-67-3 ]

[ 39489-67-3 ] Synthesis Path-Downstream 1~35

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[ 106-41-2 ]
[ 107-14-2 ]
[ 39489-67-3 ]

References: [1]Organic Letters,2003,vol. 5,p. 3333 - 3335.
[2]Bulletin de la Societe Chimique de France,1972,p. 2749 - 2755.

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[ 108-73-6 ]
[ 39489-67-3 ]
2-(4-bromophenoxy)-1-(2,4,6-trihydroxyphenyl)ethanone [ No CAS ]

References: [1]Chemistry of Natural Compounds,1998,vol. 34,p. 435 - 441.
Khimiya Prirodnykh Soedinenii,1998,p. 466 - 474.

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[ 39489-67-3 ]
[ 606966-20-5 ]

References: [1]Organic Letters,2003,vol. 5,p. 3333 - 3335.

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[ 39489-67-3 ]
4-amino-5-(4-bromophenoxy)-6-(4-bromophenoxymethyl)-1H-pyrimidin-2-one [ No CAS ]

References: [1]Organic Letters,2003,vol. 5,p. 3333 - 3335.

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[ 39489-67-3 ]
[ 606966-29-4 ]

References: [1]Organic Letters,2003,vol. 5,p. 3333 - 3335.

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[ 590-17-0 ]
[ 39489-67-3 ]

Yield	Reaction Conditions	Operation in experiment
98%		Add 4-bromophenol (5.0 g, 28.9 mmol) and potassium carbonate (12.0 g, 86.3 mmol) in acetone (100 mL) and stir for 10 minutes. Next, add bromoacetonitrile (2.4 mL, 34.7 mmol) and stir the reaction at room temperature. After 12 hours, concentrate the reaction and pour into water. Extract with ethyl acetate (3x100 mL). Wash with water (1x150 mL), and brine (1x150 mL), dry over magnesium sulfate, filter and concentrate under reduced pressure to provide crude product Purify the residue by flash chromatography (silica gel), eluting with 20% ethyl acetate: hexanes (isocratic) to provide 6 g (98%) of the desired product that is used in step B.

References: [1]Patent: WO2005/40110,2005,A1 .Location in patent: Page/Page column 103.

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[ 39489-67-3 ]
[ 26583-55-1 ]

Yield	Reaction Conditions	Operation in experiment
100%		Add the product of step A (6.0 g, 28.3 mmol) and boron dimethyl sulfide (3.1 mL, 31. 1 mmol) in THF (100 mL) and stir the reaction at refllux temperature. After 12 hours, cool and concentrate the reaction. Add saturated solution of HCl in methanol to the crude residue slowly and concentrate the solution to get the HC1 salt of the corresponding amine. Triturate with diethyl ether and dry the product to provide quantitative yield of the desired product, N-2- (4-bromo-phenoxy) ethylamine, used in step C.
80.9%	With borane-THF; In tetrahydrofuran; at 0 - 80℃; for 14h;	To a mixture of 2-<strong>[39489-67-3](4-bromophenoxy)acetonitrile</strong> (1.90 g, 8.96 mmol, 1.00 eq) in THF (20.0 mL) was added BH3.THF (1 M, 26.9 mL, 3.00 eq) in portions at 0 C., the reaction was stirred at 0 C. for 2 hours, then the reaction mixture was heated to 80 C. and stirred at 80 C. for 12 hours. After completion, the reaction mixture was quenched with MeOH (30 mL) until no gas was formed, then concentrated. The residue was purified by column chromatography (SiO2, Petroleum ether:Ethyl acetate=5:1 to Dichloromethane: Methanol=10:1) to give 2-(4-bromophenoxy)ethanamine (1.60 g, 7.26 mmol, 80.9% yield, 97.9% purity) as yellow oil. LCMS [M+1, M+3]: 216, 218.
	In tetrahydrofuran; hydrogenchloride; sodium hydroxide;	Step 2: {2-[(4-Bromophenyl)oxy]ethyl}amine To a solution of [(4-bromophenyl)oxy]acetonitrile (3.07 g; 14.5 mmol; step 1 above) in anhyd THF (10 mL) at 0 C. was added BH3.DMS (18.1 mL of a 2M solution in THF; 36.2 mmol), dropwise over 5 min. The mixture was heated under reflux for 1.5 h, cooled, and 2M HCl (ca. 50 mL) was slowly added. The acidic mixture was extracted with Et2O (2) and the extracts set aside. NaOH pellets were added to the aqueous residue until ca. pH 14, and the whole was extracted with Et2O (3). Combined extracts of the basic mixture were washed (brine), dried over Na2SO4, and concentrated in vacuo, affording the first batch of title compound as a pale yellow liquid. The reserved Et2O extracts (from acidic mixture) were concentrated in vacuo, the residue was heated at near reflux in 15 wt % NaOH (aq) for 15 min, cooled, and extracted with CH2Cl2 (3). Combined organics were washed (brine) and concentrated in vacuo. The residue was slurried in 4M HCl and insoluble material was removed by filtration. The filtrate was extracted with Et2O (2), pH was adjusted to ca. pH 14 by addition of NaOH pellets and extracted with Et2O (*5). Combined extracts from the basic mixture were washed (brine), dried over Na2SO4, filtered and concentrated in vacuo, affording a second batch of the title compound, which was combined with the first batch. LC/MS (method D) 1.15 min, m/z 216 (M+H, 79Br), 218 (M+H, 81Br).

	In tetrahydrofuran; hydrogenchloride; NaOH;	Step 2: {2-[(4-Bromophenyl)oxy]ethyl}amine To a solution of [(4-bromophenyl)oxy]acetonitrile (3.07 g; 14.5 mmol; step 1 above) in anhyd THF (10 mL) at 0 C. was added BH3.DMS (18.1 mL of a 2M solution in THF; 36.2 mmol), dropwise over 5 min. The mixture was heated under reflux for 1.5 h, cooled, and 2M HCl (ca. 50 mL) was slowly added. The acidic mixture was extracted with Et2O (2) and the extracts set aside. NaOH pellets were added to the aqueous residue until ca. pH 14, and the whole was extracted with Et2O (3). Combined extracts of the basic mixture were washed (brine), dried over Na2SO4, and concentrated in vacuo, affording the first batch of title compound as a pale yellow liquid. The reserved Et2O extracts (from acidic mixture) were concentrated in vacuo, the residue was heated at near reflux in 15 wt % NaOH (aq) for 15 min, cooled, and extracted with CH2Cl2 (3). Combined organics were washed (brine) and concentrated in vacuo. The residue was slurried in 4M HCl and insoluble material was removed by filtration. The filtrate was extracted with Et2O (2), pH was adjusted to ca. pH 14 by addition of NaOH pellets and extracted with Et2O (*5). Combined extracts from the basic mixture were washed (brine), dried over Na2SO4, filtered and concentrated in vacuo, affording a second batch of the title compound, which was combined with the first batch. LC/MS (method D) 1.15 min, m/z 216 (M+H, 79Br), 218 (M+H, 81Br).
	With dimethylsulfide borane complex; In tetrahydrofuran; at 0℃; for 1.5h;Reflux;	To a solution of [(4-bromophenyl)oxy]acetonitrile (3.07 g; 14.5 mmol; step 1 above) in anhyd THF (10 mL) at 0 C. was added BH3.DMS (18.1 mL of a 2M solution in THF; 36.2 mmol), dropwise over 5 min. The mixture was heated under reflux for 1.5 h, cooled, and 2M HCl (ca. 50 mL) was slowly added. The acidic mixture was extracted with Et2O (×2) and the extracts set aside. NaOH pellets were added to the aqueous residue until ca. pH 14, and the whole was extracted with Et2O (×3). Combined extracts of the basic mixture were washed (brine), dried over Na2SO4, and concentrated in vacuo, affording the first batch of title compound as a pale yellow liquid. The reserved Et2O extracts (from acidic mixture) were concentrated in vacuo, the residue was heated at near reflux in 15 wt % NaOH (aq) for 15 min, cooled, and extracted with CH2Cl2(×3). Combined organics were washed (brine) and concentrated in vacuo. The residue was slurried in 4M HCl and insoluble material was removed by filtration. The filtrate was extracted with Et2O (×2), pH was adjusted to ca. pH 14 by addition of NaOH pellets and extracted with Et2O (×5). Combined extracts from the basic mixture were washed (brine), dried over Na2SO4, filtered and concentrated in vacuo, affording a second batch of the title compound, which was combined with the first batch.

References: [1]Patent: WO2005/40110,2005,A1 .Location in patent: Page/Page column 103-104.
[2]Patent: US2017/183308,2017,A1 .Location in patent: Paragraph 0533.
[3]Patent: US2010/113512,2010,A1 .
[4]Patent: US2011/124559,2011,A1 .
[5]Patent: CN102516115,2016,B .Location in patent: Paragraph 0467; 0468.

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[ 39489-67-3 ]
[ 35368-49-1 ]

References: [1]Synlett,2009,p. 2338 - 2340.

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[ 106-41-2 ]
[ 590-17-0 ]
[ 39489-67-3 ]

Yield	Reaction Conditions	Operation in experiment
85.1%	With potassium carbonate; In acetonitrile; at 80℃; for 3h;	To a mixture of 4-bromophenol (2.00 g, 11.6 mmol, 1.00 eq) and 2-bromoacetonitrile (1.66 g, 13.9 mmol, 924 uL, 1.20 eq) in MeCN (30.0 mL) was added K2CO3 (3.99 g, 28.9 mmol, 2.50 eq), and the mixture was stirred at 80 C. for 3 hours. After completion, solids were removed by filtration and the filtrate concentrated. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate=I/O to 10:1) to give 2-(4-bromophenoxy)acetonitrile (2.10 g, 9.83 mmol, 85.1% yield, 99.3% purity) as white solid. (0532) 1H NMR (400 MHz, Chloroform-d) δ 7.49 (d, J=9.2 Hz, 2H), 6.90 (d, J=9.2 Hz, 2H), 4.77 (s, 2H).
	With caesium carbonate; In ethyl acetate; acetonitrile;	Step 1: [(4-Bromophenyl)oxy]acetonitrile A mixture of p-bromophenol (2.61 g; 15.1 mmol), bromoacetonitrile (1.11 mL; 15.9 mmol), and Cs2CO3 (7.40 g; 22.7 mmol) in anhyd MeCN (25 mL) was heated at 80 C., under N2 overnight. The mixture was cooled, filtered through a pad of Celite and concentrated in vacuo. The residue was dissolved in a minimal amount of EtOAc/hexanes and filtered through a short pad of silica gel (EtOAc/hexanes eluent), affording the title compound as a colorless, waxy solid which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 4.75 (s, 2H), 6.88 (m, 2H), 7.46 (m, 2H).
	With caesium carbonate; In ethyl acetate; acetonitrile;	Step 1: [(4-Bromophenyl)oxy]acetonitrile A mixture of p-bromophenol (2.61 g; 15.1 mmol), bromoacetonitrile (1.11 mL; 15.9 mmol), and Cs2CO3 (7.40 g; 22.7 mmol) in anhyd MeCN (25 mL) was heated at 80 C., under N2 overnight. The mixture was cooled, filtered through a pad of Celite and concentrated in vacuo. The residue was dissolved in a minimal amount of EtOAc/hexanes and filtered through a short pad of silica gel (EtOAc/hexanes eluent), affording the title compound as a colorless, waxy solid which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 4.75 (s, 2H), 6.88 (m, 2H), 7.46 (m, 2H).

	With sodium tris(acetoxy)borohydride; caesium carbonate; In acetonitrile; at 80℃;Inert atmosphere;	A mixture of p-bromophenol (2.61 g; 15.1 mmol), bromoacetonitrile (1.11 mL; 15.9 mmol), and Cs2CO3(7.40 g; 22.7 mmol) in anhyd MeCN (25 mL) was heated at 80 C., under N2overnight. The mixture was cooled, filtered through a pad of Celite and concentrated in vacuo. The residue was dissolved in a minimal amount of EtOAc/hexanes and filtered through a short pad of silica gel (EtOAc/hexanes eluent), affording the title compound as a colorless, waxy solid which was used without further purification.
2.40 g	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃;	Bromoacetonitrile (1 .2 mL, 17.3 mmol) was added to a stirred suspension of 4-bromophenol (2.00 g, 1 1 .6 mmol) and potassium carbonate in DMF (60 mL). Once addition was complete, the resulting mixture was heated at 50C overnight. The reaction mixture was cooled to RT, diluted with EtOAc (150 mL) and the organic layer was separated, washed with water (2 x 70 mL), brine (2 x 40 mL) then dried by passing through phase separator. The organics were concentrated in vacuo and the crude compound was purified by silica gel chromatography eluting with 0-50% EtOAc//'so- hexane to afford 2-(4-bromophenoxy)acetonitrile (2.40 g). A portion of this material (1 .00 g, 4.72 mmol) was dissolved in dry THF (20 mL) under N2 and methylmagnesium bromide (3 M in Et20, 5.5 mL, 16.5 mmol) was added dropwise. The reaction mixture was heated to 60C for 1 h, then titanium (IV) isopropoxide (1 .4 mL, 4.72 mmol) was added dropwise. The reaction mixture was stirred at 50C for 16 h. The reaction mixture was partitioned between DCM and brine. The mixture was filtered through celite and the filter cake washed with DCM. The organic fraction was separated, washed with brine again, followed by washing with aq 10% NaOH (2x) to remove the phenol starting material, dried by passing through a phase separator and evaporated to dryness to afford the desired product A43 as a brown oil (712 mg, 62%); LC-MS. Rt 1 .48 min, (0515) AnalpH2_MeCN_4min(1); (ESI+) m/z 244.0, 246.0 (M+H)+.
2.4 g	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃;	bromoacetonitrile (1.2 ml_, 17.3 mmol) was added to a stirred suspension of 4-bromophenol (2.00 g, 1 1.6 mmol) and potassium carbonate (4.80 g,34.8 mmol) in DMF (60 ml_). Once addition was complete, the resulting mixture was heated at 50C overnight. The reaction mixture was cooled to RT, diluted with EtOAc (150 ml_) and the organic layer was separated, washed with water (2 x 70 ml_), brine (2 x 40 ml_) then dried by passing through a phase separator. The organics were concentrated in vacuo and the crude compound was purified by silica gel chromatography eluting with 0-50% EtOAc//so-hexane to afford 2-(4-bromophenoxy)acetonitrile (A28) (2.40 g).

References: [1]Patent: US2017/183308,2017,A1 .Location in patent: Paragraph 0531; 0532.
[2]ACS Combinatorial Science,2014,vol. 16,p. 85 - 91.
[3]Patent: US2010/113512,2010,A1 .
[4]Patent: US2011/124559,2011,A1 .
[5]Patent: CN102516115,2016,B .Location in patent: Paragraph 0465; 0466.
[6]Patent: WO2019/73253,2019,A1 .Location in patent: Paragraph 00196.
[7]Patent: WO2020/115481,2020,A1 .Location in patent: Paragraph 00262.

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[ 1007579-11-4 ]

References: [1]Patent: US2011/124559,2011,A1 .
[2]Patent: CN102516115,2016,B .

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[ 1532533-35-9 ]