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Chemical Structure| 57045-85-9 Chemical Structure| 57045-85-9

Structure of 57045-85-9

Chemical Structure| 57045-85-9

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Product Details of [ 57045-85-9 ]

CAS No. :57045-85-9
Formula : C8H7BrClNO
M.W : 248.50
SMILES Code : CC(NC1=CC=C(Cl)C=C1Br)=O
English Name :N-(2-Bromo-4-chlorophenyl)acetamide
MDL No. :MFCD00040851

Safety of [ 57045-85-9 ]

Application In Synthesis of [ 57045-85-9 ]

* 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 [ 57045-85-9 ]

[ 57045-85-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 539-03-7 ]
  • [ 57045-85-9 ]
YieldReaction ConditionsOperation in experiment
98% With N-Bromosuccinimide In acetonitrile for 2h; Irradiation; regioselective reaction;
95% With hydrogen bromide; Selectfluor In water at 20℃; for 3.5h; regioselective reaction; II. Bromination of anilides 1 General procedure: 1a as example: To a stirred suspension of N-(p-tolyl)acetamide 1a (75 mg, 0.5 mmol) and Selectfluor (213 mg, 0.6 mmol) in water (3.0 mL) was added HBr (40% aqueous, 0.08 mL, 0.55 mmol), and the mixture was stirred for 5 min at room temperature. After 1a was consumed, as indicated by TLC, the reaction mixture was quenched with saturated aqueous Na2S2O3 (2.0 mL) and water (20.0 mL), and extracted with CH2Cl2 (10.0 mL) three times. The residue obtained after evaporation of the solvent was purified by column chromatography on silica gel (petroleum ether-ethyl acetate = 6:1, v/v) to afford N-(2-bromo-4-methylphenyl)acetamide 2a as a white solid (108 mg, 95% yield).
88% With acetic anhydride; copper(II) bis(trifluoromethanesulfonate); N-Fluorobenzenesulfonimide; sodium bromide In acetonitrile at 80℃; for 3h; Inert atmosphere; regioselective reaction;
79% With N-Bromosuccinimide; cobalt acetylacetonate; trifluoroacetic acid; silver(l) oxide In 1,2-dichloro-ethane at 60℃; for 16h; regioselective reaction;
75% With N-Bromosuccinimide; methanesulfonic acid; nickel(II) chloride hexahydrate In water at 20℃; for 5h; Sealed tube; Microwave irradiation; Green chemistry; regioselective reaction; Procedure B General procedure: A 10 mL microwave vial was charged with an anilide or carbamate derivative (1.0 equiv, 0.5 mmol), NXS (1.2 equiv, 0.6 mmol), Ag2CO3 (10 mol%, 14 mg), MSA (3.0 equiv, 1.5 mmol, 144 mg) and toluene (2.0 mL). The vial was then sealed and stirred at 50 °C, for 8 h. After the reaction time, the mixture was diluted with EtOAc and washed with sodium bicarbonate solution. The organic layer was dried with anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (n-hexane/EtOAc) to give the desired product.
69% With N-Bromosuccinimide; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; Boc-Phe-OH; silver(I) triflimide In 1,2-dichloro-ethane at 20℃; for 4h; Inert atmosphere; Sealed tube;
With perchloric acid; mercury(II) diacetate; N-bromoacetamide In water at 35℃; δE(excit.), ΔH(excit.), ΔS(excit.); further reaction partners: Cl(-), Br(-);
With hydrogen bromide; nitric acid
With bromine; sodium acetate; acetic acid at 70℃;
With water; bromine

  • 2
  • [ 873-38-1 ]
  • [ 108-24-7 ]
  • [ 57045-85-9 ]
YieldReaction ConditionsOperation in experiment
99% With dmap In chloroform for 6h; Reflux; N-Acetylation; General Procedure General procedure: In a 50-mL, round-bottom flask, aniline (5.0 mmol, 1.0 equiv) was dissolved in CHCl3 (20 mL), followed by addition of DMAP (0.031 g, 0.25 mmol, 5 mol%). Ac2O (0.51 g, 5.0 mmol, 1.0 equiv) was added dropwise, and the mixture was stirred at reflux temperature (TLC monitoring) until completion. The mixture was cooled to r.t. and washed with distilled water. The organic layer was dried (anhyd MgSO4), followed by removal of solvent under reduced pressure to obtain the crude product, which was purified by flash chromatography (EtOAc/n-hexane).
97.9% With pyridine In dichloromethane at 23℃; for 19h;
86% In dichloromethane at 20℃; 1.2.1I Preparation of N-(2-Bromo-4-chloro-phenyl)-acetamide To a stirred mixture of 2-bromo-4-chloroaniline (5 g, 24 mmol) and catalytic DMAP in CH2Cl2 (15 mL) was add acetic anhydride (2.3 mL, 24 mmol) at room temperature. The reaction mixture was stirred overnight then washed with saturated aqueous NaHCO3 solution. The CH2Cl2 layer was dried (MgSO4), filtered, concentrated in vacuo. The crude material was triturated with Hexane/Et2O and the solid filtered and dried in vacuo to give N-(2-bromo-4-chloro-phenyl)-acetamide (5.2 g, 86%). HPLC: Rt=2.26 min. m/z=248 M+H+).
at 20℃; for 1.5h; 13.1 Step 1: N-(2-Bromo-4-chlorophenyl)acetamide A solution of 2-bromo-4-chloroaniline (1 g, 4.84 mmol) in acetic anhydride (5 ml, 4.84 mmol) was stirred at RT for 1.5 hrs. The resulting suspension was collected by filtration and dried on a vacuum line to give the title compound as a white solid. (0532) LC-MS: Rt 0.90 mins; MS m/z 250.0 [M+H]+; Method 2minLowpH (0533) 1H NMR (400 MHz, DMSO-d6) δ 9.51 (1H, s), 7.78 (1H, d), 7.62 (1H, d), 7.44 (1H, dd), 2.08 (3H, s).
With dmap In chloroform at 61℃; 2.2.1 Synthesis of 2-bromo-4-chlorophenylacetamide (Cl1) In a 50ml two-necked bottle, add 2-bromo-4-chloroaniline (2.46g, 0.012mol)Dissolve in chloroform (20ml), then add 4-dimethylaminopyridine (DMAP, 73mg, 0.6mol), and then add acetic anhydride (1.24g, 0.012mol) dropwise.Stir and reflux the reaction in a 61°C oil bath for 12 hours. After the reaction is completed, cool to room temperature.Extract with dichloromethane and water three times, dry the organic phase with anhydrous magnesium sulfate, filter and spin the solvent dry.Column chromatography separates Cl1.

 

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