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Chemical Structure| 37746-78-4 Chemical Structure| 37746-78-4
Chemical Structure| 37746-78-4

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Product Details of (E)Ethyl 4-bromocrotonate

CAS No. :37746-78-4
Formula : C6H9BrO2
M.W : 193.04
SMILES Code : O=C(OCC)/C=C/CBr
MDL No. :MFCD00000247
InChI Key :FHGRPBSDPBRTLS-ONEGZZNKSA-N
Pubchem ID :5373944

Safety of (E)Ethyl 4-bromocrotonate

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501
Class:8
UN#:3265
Packing Group:

Application In Synthesis of (E)Ethyl 4-bromocrotonate

* 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 [ 37746-78-4 ]

[ 37746-78-4 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 37746-78-4 ]
  • [ 2033-42-3 ]
  • [ 111726-54-6 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetonitrile; at 20℃; for 12h; At room temperature, the intermediate WX002-2 (9 g, 33.33 mmol) was dissolved in acetonitrile (150 mL), thenpotassium carbonate (9.21 g, 66.65 mmol) and ethyl 4-bromocrotonate (6.43 g, 33.33 mmol, 4.60 mL) were addedsuccessively, and the reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction,the reaction solution was filtered, the filtrate was collected, and the filter cake was washed with ethyl acetate (30 mL 32). The filtrate and washings were combined, the solvent was removed under reduced pressure, and the resulting residuewas purified by column chromatography (eluent: petroleum ether/ethyl acetate = 1/0-20/1, volume ratio) to obtain thetarget intermediate WX002-3. 1H NMR (400 MHz, CDCl3) δ: 8.17 (d, J = 8.4 Hz, 1H), 7.81 (d, J = 8.8 Hz, 1H), 7.75 (d,J = 8.0 Hz, 1H), 7.57 (ddd, J = 1.2, 7.0, 8.5 Hz, 1H), 7.42 (ddd, J = 1.1, 6.9, 8.1 Hz, 1H), 7.19-7.10 (m, 2H), 6.46 (td, J= 2.1, 15.7 Hz, 1H), 4.90 (dd, J = 2.0, 3.6 Hz, 2H), 4.25 (q, J = 7.2 Hz, 2H), 1.33 (t, J = 7.1 Hz, 3H).
  • 2
  • [ 37746-78-4 ]
  • [ 6940-80-3 ]
  • ethyl (S)-(+)-5-benzyl-7-hydroxy-6-methyl-5-aza-2-heptenoate [ No CAS ]
  • 3
  • [ 37746-78-4 ]
  • [ 102831-44-7 ]
  • [ 192636-66-1 ]
  • 4
  • [ 36822-11-4 ]
  • [ 37746-78-4 ]
  • 7-phenyl-2,3-dihydro-5-oxo-5H-thiazolo-[3,2-a]pyrimidine-3-acetate [ No CAS ]
  • 5
  • [ 37746-78-4 ]
  • [ 105580-41-4 ]
  • [ 125991-45-9 ]
YieldReaction ConditionsOperation in experiment
With iodine; In benzene-ether-tetrahydrofuran; water; REFERENCE EXAMPLE 17 Production of ethyl 5-[4-(tert-butoxycarbonyl)-phenyl]hexanoate: In a solution of <strong>[105580-41-4]ter<strong>[105580-41-4]t-butyl 4-acetylbenzoate</strong></strong> (19.90 g) in a benzene-ether-tetrahydrofuran mixture (3:3:2, 200 ml) was suspended zinc (11.81 g), to which ethyl 4-bromocrotonate (17.44 g) was added slowly while heating and stirring, and then iodine (about 20 mg) was added. The resulting mixture was refluxed by heating on an oil bath (60-70 C.) for 1 hour, then ethyl 4-bromocrotonate (3.00 g) was added, and the mixture was further refluxed by heating for 15 minutes. After cooling to room temperature, the reaction mixture was added to water (500 ml), adjusted to pH 4.9 by addition of acetic acid and extracted with ether. The extract was washed with 5% aqueous ammonia and dried with anhydrous magnesium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography (carrier; silica gel, 300 g, developing solvent; ethyl acetate-hexane=1:5), to give the object compound. IR (Neat): 3480, 2975, 1720, 1700, 1650, 1605 cm-1. 1 H--NMR (CDCl3) delta: 1.20 (3H,t,J=7Hz), 1.53 (12H,s), 2.64 (2H,d,J=7Hz), 2.67 (1H,brs),3.63 (3H,s), 4.08 (2H,q,J=7Hz), 5.80 (1H,d,J=15Hz), 6.80 (1H,dt,J=15Hz,7Hz), 7.45 (2H,d,J=8Hz), 7.90 (2H,d,J=8Hz).
  • 6
  • [ 37746-78-4 ]
  • [ 138113-08-3 ]
  • 6-((7-methoxynaphthalen-1-yl)methyl)pyridin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% General procedure: A solution of TMSCl (3 mol%) in anhyd 1,4-dioxane (1 mL) wasadded to a suspension of Zn dust (2 equiv) in anhyd 1,4-dioxane(3 mL), and the resulting suspension was refluxed with vigorousstirring for 25 min. The appropriate nitrile (2 mmol) in dry 1,4-dioxane (1 mL) and ethyl (E)-4-bromobut-2-enoate (12; 2equiv) in dry 1,4-dioxane (1 mL) were simultaneously addeddropwise to the refluxing suspension during 10 min by usingtwo syringes. The resulting light-green mixture was refluxeduntil all the starting material was consumed and the colorchanged to brown (TLC; 3-6 h). The mixture was cooled to r.t.then centrifuged (700 rpm). The upper solution was decantedand the remaining solid was washed with 1,4-dioxane (4 × 1mL). The 1,4-dioxane solutions were combined and concentratedto about 1 mL under reduced pressure in a rotatory evaporator.The residue was treated with 50% aq K2CO3 until the pHreached 13 (~5 mL). The resulting mixture was stirred for 30min at r.t. (30 C) then diluted with CH2Cl2 (10 mL) and H2O (10mL). The organic layer was separated, washed sequentially withH2O (2 × 10 mL) and brine (10 mL), dried (Na2SO4), and evaporatedunder reduced pressure to give a crude product that waspurified by column chromatography [silica gel (100-200 mesh);15-60% EtOAc-hexane].
  • 7
  • [ 37746-78-4 ]
  • [ 13599-12-7 ]
  • ethyl 4-hydroxy-2-phenylpyrazolo[1,5-a]pyridine-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With potassium carbonate; In ethanol; at 78℃; for 8h; General procedure: To a 50-mL round-bottomed flask were added ethyl pyrazole-5-carboxylate 1 (1.00 mmol), ethyl 4-bromobut-2-enoate 2 (2.00 mmol), potassium carbonate (0.28 g, 2.05 mmol) and C2H5OH (20 mL). The mixture was refluxed for 8 h. And then they were poured into water (100 mL) and extracted with CH2Cl2 (3 × 30 mL). The combined extracts were washed with water, dried over anhydrous Na2SO4 and filtered, and the solvent was removed by rotary evaporation. The crude products were purified by column chromatography to afford compounds 3a-f in 42-60percent.
 

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