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Chemical Structure| 26583-55-1 Chemical Structure| 26583-55-1

Structure of 2-(4-Bromophenoxy)ethanamine
CAS No.: 26583-55-1

Chemical Structure| 26583-55-1

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Product Details of [ 26583-55-1 ]

CAS No. :26583-55-1
Formula : C8H10BrNO
M.W : 216.08
SMILES Code : BrC1=CC=C(OCCN)C=C1
MDL No. :MFCD09064752

Safety of [ 26583-55-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501
Class:8
UN#:3259
Packing Group:

Application In Synthesis of [ 26583-55-1 ]

* 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 [ 26583-55-1 ]

[ 26583-55-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 39489-67-3 ]
  • [ 26583-55-1 ]
YieldReaction ConditionsOperation 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.

 

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