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Chemical Structure| 22118-09-8 Chemical Structure| 22118-09-8

Structure of 22118-09-8

Chemical Structure| 22118-09-8

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Product Details of [ 22118-09-8 ]

CAS No. :22118-09-8
Formula : C2H2BrClO
M.W : 157.39
SMILES Code : O=C(Cl)CBr
MDL No. :MFCD00000724
InChI Key :SYZRZLUNWVNNNV-UHFFFAOYSA-N
Pubchem ID :89602

Safety of [ 22118-09-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314-H335
Precautionary Statements:P261-P280-P305+P351+P338-P310
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 22118-09-8 ]

* 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 [ 22118-09-8 ]

[ 22118-09-8 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 110-91-8 ]
  • [ 22118-09-8 ]
  • [ 40299-87-4 ]
YieldReaction ConditionsOperation in experiment
28% With triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere; Under the protection of argon, Weigh morpholine (600 muL, 6.9 mmol) in anhydrous dichloromethane (8 mL), Triethylamine (960 muL, 6.9 mmol) was sequentially added dropwise at 0 C. A solution of 2-bromoacetyl chloride (580 muL, 6.9 mmol) in anhydrous dichloromethane (4 mL), Stir overnight at room temperature. After the reaction was completed, water (15 mL) was added to the reaction solution. Extracted with dichloromethane (15 mL x 2), Washed with saturated sodium bicarbonate (8mL x 2) and saturated sodium chloride (10mL x 1), Dry over anhydrous sodium sulfate and evaporate the solvent under reduced pressure. The residue containing compound 97-1 was used directly in the next step without further reaction.
With triethylamine; In dichloromethane; at -25 - 20℃; for 4.75h;Inert atmosphere; flask is charged with bromoacetyl bromide (25 mL), dichloromethane (500 mL) and mixture is stirred under nitrogen atmosphere. The reaction mixture is cooled to -25C followed by slow addition of morpholine (72.7 mL in 500 mL of DCM) at the same temperature over a period of 30 minutes. The reaction mixture is stirred at -25C for 15 minutes, then allowed to attain room temperature at which it is further stirred for 4 hours. The completion of the reaction is monitored by TLC and reaction mixture is sequentially washed with water (2x250 mL) and brine solution (2x100 mL). The organic solvent is subjected to distillation to afford the title compound.
  • 2
  • [ 22118-09-8 ]
  • [ 1986-47-6 ]
  • [ 133941-07-8 ]
  • 3
  • [ 22118-09-8 ]
  • [ 6519-67-1 ]
  • [ 160061-62-1 ]
  • 5
  • [ 22118-09-8 ]
  • [ 98-16-8 ]
  • [ 25625-57-4 ]
YieldReaction ConditionsOperation in experiment
64% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 1h; 3-Trifluoromethylaniline (1.6 g, 10 mmol) was dissolved in dichloromethane with DIEA (3.4 mL, 20 mmol), cooled to 0 C, and to this solution bromoacetyl chloride was added as a neat liquid (exothermic). After 1 hour the reaction mixture was washed with IN HCl, dried and concentrated to a brown oil which was purified by column chromatography (10 to 40 % EtOAc/liexanes) to give a light brown oil, 1.8 g, 6.4 mmol, 64% YIELD. 1H NMR (500 MHz, CDC13) S 8. 19 (S, 1H), 7.75 (s, 1H), 7.68 (d, J = 8.1 Hz, 1H), 7.41 (t, J = 7.9 Hz, 1H), 7.35 (d, J = 7.8 HZ,, 3. 96 (s, 2H).
  • 6
  • [ 22118-09-8 ]
  • [ 66655-67-2 ]
  • 6-(Bromoacetyl)-3,4-dihydro-2(1H)-quinazolinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride;aluminium trichloride; In carbon disulfide; Step 1 6-(Bromoacetyl)-<strong>[66655-67-2]3,4-dihydro-2(1H)-quinazolinone</strong> Bromoacetyl chloride (6.2 g) is added dropwise to a stirring mixture of <strong>[66655-67-2]3,4-dihydro-2(1H)-quinazolinone</strong> (2.6 g) and anhydrous aluminum chloride (6.3 g) in carbon disulfide (60 ml). The reaction mixture is stirred under reflux for 4.5 hours, the carbon disulfide decanted, and the residue treated with HCl (6N). The resulting solid is poured into ice water, filtered, the filtered solid washed with water and dried in vacuo, affording the desired product, which is used in the next step without further purification.
  • 7
  • [ 22118-09-8 ]
  • [ 1022-13-5 ]
  • N-methyl-(2-benzoyl-4-chloro)-phenyl bromoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% In ethyl acetate; Petroleum ether; benzene; (d) Production of N-methyl-(2-benzoyl-4-chloro)-phenyl bromoacetamide A solution of 2-methylamino-5-chlorobenzophenone in a mixture of 200 cc of benzene and 100 cc of ether is chilled to 0° C., followed by the dropwise addition over a period of 25 minutes of 5.8 cc of bromoacetyl chloride in solution in 40 cc of ether. After standing overnight while stirring at room temperature, the mixture is evaporated to dryness. The oily residue triturated in petroleum ether crystallises rapidly. The crystals are filtered, washed with petroleum ether, dissolved in ethylacetate and decoloured with animal charcoal. After filtration and concentration, precipitation with petroleum ether and filtration, 19.3 g of product are recovered. Yield: 82percent. Melting point: 90° C. Plate chromatography: support: silica gel 60 F 254 Merck solvent: ethylacetate/petroleum ether 25/75 development: UV and iodine Rf: 0.43.
  • 8
  • [ 22118-09-8 ]
  • [ 120351-94-2 ]
  • N-[2-(3-cyanophenoxy)ethyl]bromoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; Step 1 Synthesis of N-[2-(3-cyanophenoxy)ethyl]bromoacetamide: 1.50 g (9.26 mmol) of <strong>[120351-94-2]3-(2-aminoethoxy)benzonitrile</strong> and 1.77 ml (10.2 mmol) of diisopropylethylamine were dissolved in 15 ml of tetrahydrofuran. A solution of 0.92 ml (11.1 mmol) of bromoacetyl chloride in 5 ml of tetrahydrofuran was added to the obtained solution at 0C, and they were stirred for 8 hours. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound: Yield: 2.18 g (7.73 mmol) (83 %) MS (ESI, m/z) 305 (M+Na+) H-NMR (CDCl3) delta 3.76(2H, dt), 3.98 (2H, d), 4.08(2H, t), 7.14 (1H, dd),7.16 (1H, s), 7.28 (1H, dd), 7.39 (1H, td)
  • 9
  • [ 22118-09-8 ]
  • [ 1404048-56-1 ]
  • [ 131922-05-9 ]
  • [ 1403897-05-1 ]
YieldReaction ConditionsOperation in experiment
Example 113: 1 -{6-Benzyl-3,3-dimethyl-1 H,2H,3H-pyrrolo[3,2-c]pyridin(trifluoromethyl)piperazin-l -yl]ethan-1 -oneA solution of bromoacetyl chloride (0.535 g, 3.4 mmol) in DCM (5 mL) was added to a two phase mixture of 6-benzyl-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine (0.467 g, 1 .7 mmol) sodium hydrogen carbonate (1 .43 g, 17 mmol), DCM (20 mL) and water (25 mL) with ice cooling over 0.1 h. The mixture was stirred at -0 C for 2 h then the organic phase was separated and the aqueous phase was extracted with DCM (25 mL). The combined organic phases were dried (Na2S04) and evaporated in vacuo to give an oil which was purified by chromatography (Si02, 20 - 50% EtOAc in petrol) gave an oil which solidified. A mixture of this material (0.081 g, 0.23 mmol) 2-trifluoromethylpiperazine (0.039 g, 0.25 mmol), potassium carbonate (0.064 g, 0.46 mmol) and acetonitrile (2 mL) was stirred at 20 C for 4 h. The mixture was partitioned between water (30 mL) and DCM (3 x 20 mL) and the combined extracts were dried (Na2S04) and evaporated in vacuo to give an oil.Chromatography (Si02, 0 - 20% MeOH in EtOAc),gave impure product and this was followed by further chromatography (Si02, 0 - 5% MeOH in EtOAc) then preparative HPLC (basic method) to give the title compound (0.005 g). 1H NMR (Me-d3-OD): 8.24 (1 H, s), 7.94 (1 H, s), 7.34-7.23 (4H, m), 7.23-7.16 (1 H, m), 4.1 1 (2H, s), 4.03-3.92 (2H, m), 3.45 (3H, s), 3.08 (1 H, d), 3.04-2.81 (3H, m), 2.32 (2H, q), 1.42 (6H, s). MS: [M+H]+ = 433.
  • 10
  • [ 22118-09-8 ]
  • [ 1022-13-5 ]
  • [ 439-14-5 ]
  • 12
  • [ 22118-09-8 ]
  • [ 23357-46-2 ]
  • [ 630126-70-4 ]
YieldReaction ConditionsOperation in experiment
With dmap; In dichloromethane; at 0 - 25℃; for 4.5h;Inert atmosphere; Bromoacetyl chloride (0.425 mL, 5.1 mmol) in dry dichloromethane (5 mL) was added dropwise to a solution containing the respective amine (4.1 mmol) and a catalytic amount of dimethylaminopyridine (DMAP) (0.150 g, 30 mmol %) in dry dichloromethane (20 mL) maintained in an ice bath under argon atmosphere. The resulting solution was stirred at 0 C for 30 min, and the temperature was then increased to 25 C. After stirring for additional 4 hours, the reaction mixture was diluted with diethyl ether (50 mL). All of the stirring time was accomplished under an argon atmosphere. The organic layers were washed sequentially with a solution of 1 N HCl (2 × 50 mL), water (1 × 100 mL), saturated aqueous NaHCO3 (3 × 50 mL), and brine (5% w/v, 1 × 50 mL). Finally, the organic solution was dried over anhydrous MgSO4 and evaporated under vacuum, and the residue was purified by flash chromatography on silica gel and eluted with chloroform-methanol (40:1).
  • 14
  • [ 22118-09-8 ]
  • [ 436-77-1 ]
  • 7-O-(2-bromoacetate) fangchinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With dmap; In dichloromethane; at 0 - 20℃;Inert atmosphere; General procedure: Acyl chloride (0.18 mmol, 1.1 eq) was added at 0 C to a solution of <strong>[436-77-1]fangchinoline</strong> (100 mg, 0.16 mmol) and DMAP (0.032 mmol, 0.2eq) in 2 mL dry CH2Cl2 under argon and stirred for 2-4 h. The reaction mixture was quenched with a saturated aqueous solution of sodium bicarbonate and extracted three times with CH2Cl2. The combined organic phase was dried over anhydrous magnesium sulfate before vacuum suction filtration. The removal of the solventin vacuo afforded the crude product, which was chromatographied on silica gel (CH2Cl2/MeOH, 50/1 v/v, 0.1% TEA) to provide the pureproduct 1a-1e, 2a-2g, 3a-3e and 4a-4h.
 

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