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Chemical Structure| 100-19-6
Chemical Structure| 100-19-6
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Product Details of [ 100-19-6 ]

CAS No. :100-19-6 MDL No. :MFCD00007355
Formula : C8H7NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :YQYGPGKTNQNXMH-UHFFFAOYSA-N
M.W :165.15 Pubchem ID :7487
Synonyms :

Calculated chemistry of [ 100-19-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.46
TPSA : 62.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : 1.53
Log Po/w (WLOGP) : 1.8
Log Po/w (MLOGP) : 0.59
Log Po/w (SILICOS-IT) : -0.01
Consensus Log Po/w : 1.05

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.07
Solubility : 1.42 mg/ml ; 0.00859 mol/l
Class : Soluble
Log S (Ali) : -2.46
Solubility : 0.573 mg/ml ; 0.00347 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.11
Solubility : 1.29 mg/ml ; 0.00783 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.38

Safety of [ 100-19-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 100-19-6 ]

* 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.

  • Upstream synthesis route of [ 100-19-6 ]
  • Downstream synthetic route of [ 100-19-6 ]

[ 100-19-6 ] Synthesis Path-Upstream   1~29

  • 1
  • [ 100-19-6 ]
  • [ 58431-12-2 ]
  • [ 611-08-5 ]
  • [ 100-19-6 ]
Reference: [1] Journal of Physical Chemistry, 1986, vol. 90, # 19, p. 4648 - 4650
  • 2
  • [ 288-32-4 ]
  • [ 100-19-6 ]
  • [ 2301-25-9 ]
Reference: [1] European Journal of Organic Chemistry, 2011, # 14, p. 2692 - 2696
  • 3
  • [ 100-19-6 ]
  • [ 99-81-0 ]
YieldReaction ConditionsOperation in experiment
99% With copper(ll) bromide In ethyl acetate at 60 - 65℃; for 8 h; 2-1-1:
Preparation of α-bromo-4-nitroacetophenone
5 g (30.3 mmol) of 4-nitroacetophenone was dissolved in 150 ml of ethyl acetate and 13.5 g (60.6 mmol) of copper (II) bromide was added thereto, followed by stirring at a temperature of 60 to 65° for 8 hours.
After the reaction was complete, the reaction liquid was cooled to room temperature and the salt formed during the reaction was filtered off The filtrate was washed three times with a sodium bicarbonate saturated solution.
This solution was dried over anhydrous magnesium sulfate, filtered under reduced pressure, distilled under reduced pressure and then dried under vacuum at about 40° to afford 7.3 g (yield: 99percent) of the desired compound which was then directly subjected to the subsequent reaction.
Mass (M+): 245.1
99% With copper(ll) bromide In ethyl acetate at 60 - 65℃; for 8 h; Example 2-1-1 Preparation of a-bromo-4-nitroacetophenone 5g (30.3mmol) of 4-nitroacetophenone was dissolved in 150ml of ethyl acetate and 13.5g (60.6mmol) of copper (II) bromide was added thereto, followed by stirring at a temperature of 60 to 65°C for 8 hours. After the reaction was complete, the reaction liquid was cooled to room temperature and the salt formed during the reaction was filtered off. The filtrate was washed three times with a sodium bicarbonate saturated solution. This solution was dried over anhydrous magnesium sulfate, filtered under reduced pressure, distilled under reduced pressure and then dried under vacuum at about 40°C to afford 7.3g (yield: 99percent) of the desired compound which was then directly subjected to the subsequent reaction. Mass (M+): 245.1
95% With aluminum (III) chloride; bromine In diethyl ether at 0 - 20℃; for 3 h; To a solution of 4-nitroacetophenone (30 g, 0.18 mol) in dry ether(500 mL) stirred at 0 oC, was added AlCl3 (cat), followed by Br2(10.3 mL, 0.20 mol). The reaction mixture was stirred at rt fot 3h. Then the reaction was quenched with Na2S2O3-NaHCO3 (aq),extracted with DCM (400 mL*2), the combined organic phase waswashed with brine, dried over Na2SO4, filtered and concentratedto give the title compound as yellow solid (42 g, 95percent); 1H-NMR(300 MHz, CDCl3): δ 8.36–8.33 (m, 2H), 8.17–8.14 (m, 2H), 4.46 (s,2H); LRMS (ESI) m/z 244 [M+H]+; mp 76–79 oC.
94% With bromine In diethyl ether at 20℃; for 2 h; Cooling with ice To a solution of 1 (1.65 g, 10 mmol) in dry ethylether (150 mL) was added Br2 (1.60 g, 10 mmol) dropwise in an ice bath. The reaction mixture was stirred at room temperature for 2 h. Evaporation of the solvent afforded 2.29 g of 2 as a white crystal (94percent). 1H NMR (400 MHz, CDCL3) δ 8.35 (d, J = 9.1 Hz, 2H), 8.15 (d, J = 9.1 Hz, 2H), 4.47 (s, 2H).
89% With N-Bromosuccinimide; tetrachlorosilane In acetonitrile at 20℃; for 7 h; General procedure: To a mixture of NXS and substrate (1 or 6) in CH3CN at room temperature was added SiCl4 and the mixture left to stir until TLC showed the disappearance of the starting material. The reaction was then poured onto H2O and the mixture extracted with CH2Cl2. The extracts were combined, dried over MgSO4 and evaporated. The residue was purified by recrystallization (pet. ether-Et2O, 3:1) to give pure 2b-2g, 3b, or by silica gel column chromatography (hexane-EtOAc 10:1 or 30:1) to give pure 2a,h,i, 3a-5 or 7-9, respectively
88% With N-Bromosuccinimide; toluene-4-sulfonic acid In acetonitrile at 50℃; for 24 h; In a 500 ml single-port the bottle, the nitro-acetophenone (63.74g, 386mmol), N-bromo succinimide (68.77g, 386 . 4mmol), P-toluene sulfonic acid monohydrate (73.33g, 386mmol) and acetonitrile 200 ml, in the 50 °C reaction under 24 hours. TLC shows the reaction is complete, solvent is removed under reduced pressure, the residue add saturated sodium bicarbonate solution and to neutral, extraction with ethyl acetate, the organic phase is dried with anhydrous sodium sulfate, evaporated under reduced pressure, washed with petroleum ether, to obtain yellow solid (82.9g, 88.0percent).
82% at 670℃; for 6 h; Green chemistry The representative example of oxidative bromination is described as follows: A mixture of 1.2 g acetophenone 1a (10 mmol) and 0.121 g Cu(NO3)2•3H2O (0.5mmol) was stirred and an oxygen balloon (about 0.5–1 L) was attached to the reaction system. Then 8mol/L aqueous solution of hydrobromic acid (1.5mL, 12mmol) was added dropwise to the mixture. The reaction mixture was then stirred at 70°C and monitored by TLC or GC. After the completion of the reaction, the mixture was extracted with CH2Cl2. The organic extract was first washed with 5percent sodium sulfite, saturated sodium bicarbonate solution, and then water and finally dried over anhydrous magnesium sulfate. The solvent was removed under vacuum and the residue was purified by column chromatography (silica gel, petroleum ether/dichloromethane 3:1) to afford the product, α-bromoacetophenone (2a) in 1.81 g, yield: 91percent.
81.96% With aluminum (III) chloride; bromine In chloroform at 45℃; 4-Nitroacetophenone (16.5 g, 0.1 mol) was dissolved in 50 ml ofchloroform and to this, 200 mg of anhydrous aluminum trichloride(AlCl3) was added at once. It was then kept for stirring at around45 °C. A bromine solution (0.15 mol), which was previously dilutedin chloroform 20 ml, was added drop-wise for 1 h. The completionof reaction was confirmed by TLC. The solvent was removed underreduced pressure. The residual solid was filtered and crystallizedfrom methanol and afforded 20.0 g (81.96percent yields) of 1.
81% With bromine In chloroform at 0 - 20℃; for 16 h; General procedure: A solution of bromine (2.90 g, 18.0 mmol) in chloroform (150 mL) was slowly added to a cooled solution (0 °C) of acetophenone 1b–c (17.0 mmol) in chloroform (150 mL), over a period of 1 h, the mixture stirred at room temperature for 15 h and quenched with ice-cold water. The organic layer was washed with saturated sodium bicarbonate solution, water and brine. The organic phase was dried over anhydrous sodium sulfate, concentrated under vacuum and purified on a silica gel (100–200 mesh) column. Elution with hexane–ethyl acetate (9 : 1) yielded pure compounds 2b and 2c.
80% With sulfuric acid; bromine; nitric acid; potassium iodide In chlorobenzene at 40 - 60℃; for 3.5 h; p-Nitroacetophenone (10.0g, 60.6mmol), H2SO4 (10mL, 6M), HNO3 (7.0mL, 3M), KI (0.50g,3.0 mmol) chlorobenzene (100 mL) was added to a three-necked flask, stirred and dissolved, and Br2 (1.60 mL, 31 mmol) was added dropwise at 40 ° C.After 0.5h,The mixture was heated to 60 ° C with heating and stirring, and after 3 hours of reaction, the reaction was stopped, and the mixture was allowed to stand and then layered.The upper aqueous phase is poured into the reaction bottle for recycling, and the lower organic phase is washed with sodium hydrogen sulfite solution, washed with sodium hydrogen carbonate solution, dried, and analyzed by HPLC, p-nitroacetophenone: α-bromo-p-nitrophenyl Ketone: The molar ratio of α,α-dibromo-p-nitroacetophenone is 5:88.2:6.8.The organic phase was desolvated under reduced pressure and recrystallized to give α-bromo-p-nitroacetophenone, 11.85 g, yield 80percent.
79.6% at 0 - 20℃; for 2 h; General procedure: To a solution of 4-substitutedacetophenone (0.3 mol) and acetic acid (75 mL), added drop-wise bromine (20 mL) in acetic acid (75 mL). The contentswere stirred for 1 h at 0-10 °C and further for 1 h at room tempe-rature. Then the reaction mixture was poured into crushed ice,the solid separated was filtered and washed with water [21,22].The product was recrystallized from methanol. R f was deter-mined in a solvent mixture of n-hexane and ethyl acetate (7:3).
71% With N-Bromosuccinimide; toluene-4-sulfonic acid In dichloromethaneIrradiation General procedure: In a dry tube, substituted acetophenone (2 mmol), NBS (2 mmol) and PTSA (0.2 mmol, 10 molpercent) were added. 3-4 ml of anhydrous DCM was added and the tube was then irradiated in ultrasonic both till the completion of reaction (TLC). The reaction mixture was then cooled and extracted with 3 x 10 ml quantities of DCM. Organic layers were separated, dried over anhydrous MgSO4 and finally purified by silica gel chromatography [16].
69% With bromine In diethyl ether for 0.666667 h; 4-Nitroacetophenone (25 g) in ether (250 ml) was treated with aluminium chloride (catalytic amount) followed by bromine (7.77ml) for 10 minutes and the reaction was stirred for 30 minutes. The reaction was quenched with aqueous NaHCC>3, the ether layer was separated, dried using Na2S04 and concentrated. The residue was dissolved in EtOAc, dried using Na2S04, and concentrated to get off white solid which was crystallized in EtOAc/ Pet ether to yield 25.5gm (69percent) of the title compound. ^NMR (CDC13, 300MHz): δ 8.19 (d, 2H), 8.36 (d, 2H), 4.47 (s, 2H).
69% for 0.666667 h; Example 1 :2-Bromo-1-(4-nitrophenyl)ethanone4-Nitroacetophenone (25 g) in ether (250 mL) was treated with aluminium chloride (catalytic amount) followed by bromine (7.77 mL) over 10 min and the reaction was stirred for 30 min. The reaction was quenched with aqueous sodium bicarbonate, the ether layer was separated, dried over anhydrous Na2S04 and concentrated to yield a residue. The residue obtained was crystallized using ethyl acetate and petroleum ether to afford the title compound (according to the procedure described in US4812470). Yield: 25.5 g (69 percent); 1 H NMR (CDCI3, 300MHz): δ 8.19 (d, 2H), 8.36 (d, 2H), 4.47 (s, 2H).
69% With aluminum (III) chloride; bromine In diethyl ether at 20℃; for 0.666667 h; A solution of 4-nitroacetophenone (25 g, 151 mmol, 1.0 equiv) in ether (250 ml) was treated with catalytic amount of aluminum chloride followed by bromine (7.77 ml, 151 mmol, 1.0 equiv) over 10 min and the reaction was stirred for an additional 30 min. The reaction was then quenched with aqueous sodium bicarbonate, the ether layer separated, dried over sodium sulfate, and evaporated under reduced pressure. The residue was crystallized using ethyl acetate and petroleum ether to afford the title compound (25.5 g, 69percent).1H NMR (CDCl3, 300 MHz) δ 8.39-8.36 (d, J = 8.7 Hz, 2H), 8.19-8.16 (d, J = 8.7 Hz, 2H), 4.48 (s, 2H); MS (ESI-) m/z 243 [M - H]-, MS (ESI+) m/z 245 [M + H]+.
69% With aluminum (III) chloride; bromine In diethyl ether for 0.666667 h; Inert atmosphere To a solution of 4-Nitroacetophenone (25.0 g, 151 mmol,1.0 equiv) in ether (250 ml) bromine (7.77 ml, 151 mmol, 1.0 equiv) was added over 10 min. The reaction mixture was stirred for 30 minin the presence of catalytic amount of aluminum chloride (1.0 g,7.5 mmol, 0.05 equiv). Following reaction completion the reaction mixture was quenched with aqueous sodium bicarbonate. The ether layer was separated and dried over sodium sulfate and evaporated under reduced pressure. The off white residue thus obtained was crystallized in EtOAc:Pet ether to afford the title compound (25.5 g, 69percent).
63% With N-Bromosuccinimide In ethyl acetate at 40℃; In a 100 mL round bottom flask, 10 mmol of 4-nitroacetophenone and 11 mmol of N-bromosuccinimide (NBS) were added.35mL of ethyl acetate dissolved,1 g of Amberlyst 15 Ion Exchange Resin was added as a catalyst, and the reaction liquid was heated to 40°C.reaction. After TLC tracking reaction, the reaction solution was filtered to remove Amberlyst 15 ion exchange resin, and the filtrate was spin-dried.Separation (eluent: petroleum ether/ethyl acetate) gave a pale yellow solid with a yield of 63percent.
63% With N-Bromosuccinimide In ethyl acetate at 40℃; 10 mmol 4-nitroacetophenone is added to a 100 mL round bottom flaskAnd 11mmol of N-bromosuccinimide (NBS),35mL of ethyl acetate dissolved,Then add 1g of Amberlyst 15 ion exchange resin as catalyst.The reaction was warmed to 40°C and reacted.After TLC tracking reaction, the reaction solution was filtered to remove Amberlyst 15 ion exchange resin.The filtrate was spin-dried and separated by column chromatography (eluent: petroleum ether/ethyl acetate) to give a pale yellow solid with a yield of 63percent.
62% With aluminum (III) chloride; bromine In diethyl ether at 20℃; for 1.66667 h; To a solution of 4-nitroacetophenone (50g, 302mmol, 1.0equiv) in diethyl ether (500ml) was added catalytic amount of aluminum chloride (2g, 15mmol, 0.05equiv) and the reaction mixture was stirred for 10min. To this bromine (15.4ml, 302mmol) was added using an addition funnel over 30min at rt and the resulting mixture was stirred for 1h. Following reaction completion the reaction mixture was quenched using aqueous sodium bicarbonate. The ether layer was separated, dried over sodium sulfate, and evaporated under reduced pressure. The solid thus obtained was recrystallized using ethyl acetate and petroleum ether to afford the title compound (43g, 62percent). (0040) 1H NMR (CDCl3, 300MHz) δ 8.36 (d, J=8.1Hz, 2H), 8.18 (d, J=8.1Hz, 2H), 4.48 (s, 2H); Mass (ESI+) m/z 245.0 [M+H]+.
62% With tetra-N-butylammonium tribromide In methanol at 220℃; for 4 h; 1-(4-Nitropheny)ethanone (1.0 g, 6.05 mmol) and tetra-nbutylammoniumtribromide (3.82 g, 7.96 mmol) were takenin methanol (100 mL). The reaction was stirred at room temperatureovernight. The solvent was then removed under reducedpressure and the residue was dissolved in AcOEt (60 mL).The mixture was washed twice with water (2 × mL) and oncewith brine. The organic solution was then dried over Na2SO4and the solvent from the filtrate was removed. The crude product was purified using FCC (hexane-CH2Cl2) (1:1 v/v + 2 percentAcOEt), yielding the desired product as a yellow solid (0.970g, 4.47 mmol, 62 percent). δH (400 MHz; DMSO; Me4Si): δ 8.34(2H, d, J = 8.8 Hz, CH), 8.21 (2H, d, J = 8.8 Hz, CH), 5.01(2H, s, CH2Br). δC (100 MHz; DMSO; Me4Si): 191.40 (-CO-),150.61 (C), 139.13 (C), 130.60 (C), 124.38 (C), 34.79 (-CH2Br-).
37% With bromine In chloroform at 0 - 20℃; for 2 h; General procedure: To a solution of 8.40 ml (64.70 mmol) 1-(4-chlorophenyl)-ethanone (A,
Scheme 2
) in 40 ml chloroform, 3.33 ml bromine (64.7 mmol) in 10 ml chloroform were added drop wise at 0 °C.
The mixture was stirred at room temperature for 2 h and was washed with H2O (3 * 50 ml) and saturated Na2S2O3 solution (2 * 50 ml).
The organic phase was dried over Na2SO4, filtered and the solvent was removed in vacuum.
The crude product, 2-bromo-1-(4-chlorophenyl)ethanone (B,
Scheme 2
), was recrystallized from petrolether and gave 14.20 g of a white crystalline solid, yield: 92percent.

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  • 4
  • [ 100-19-6 ]
  • [ 21566-36-9 ]
  • [ 99-81-0 ]
YieldReaction ConditionsOperation in experiment
47% With N-Bromosuccinimide; silica gel In methanol for 0.25 h; Reflux General procedure: The α-bromination reaction was carried out using acetophenone (1200 mg, 10 mmol), N-bromosuccinimide (2136 mg, 12 mmol), 10percent (w/w) silica gel (120mg) in 10 mL of methanol at reflux conditions until the disappearance of the substrate. (Note: 2136mg of N-bromosuccinimide was added portion wise i.e. 356 mg for each time in six portions). The progress of the reaction was monitored by TLC. The reaction mass was filtered after the completion of the reaction as per TLC and the catalyst was collected for reuse. The filtrate was concentrated under vacuum. Double distilled water was added to the reaction mixture and quenched with aqueous sodium thiosulfate and the product extracted with dichloromethane (Caution: Severe burning sensation of eyes was observed during the work-up process). The layers were separated and the organic layer was collected and washed thrice with distilled water (3×50mL). The collected organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The obtained crude product was purified by column chromatography over silica gel (60–120 mesh) using n-hexane–EtOAc (99:1 ratio). With the aim of studying the recycling of the catalyst, the isolated catalyst was washed with ethyl acetate (5mL) after its filtration from the reaction medium, collected and dried in vacuum at 70°C to a constant weight. Subsequently it was reused for the α-bromination of acetophenone and achieved 95percent, 86percent and 83percent yields of product (2a) for first, second and third reuse of catalyst respectively. All products gave spectroscopic data in agreement with the literature [15,21,27–30]. The method is also very practical for scale up in process development. We attempted large scale (100 gram scale) synthesis of 2-bromo-1-phenylethanone 2a and obtained fruitful results with isolated yields ranging from 93percent to 96percent.
Reference: [1] Chinese Chemical Letters, 2014, vol. 25, # 1, p. 179 - 182
[2] Tetrahedron Letters, 2006, vol. 47, # 3, p. 291 - 293
  • 5
  • [ 67-56-1 ]
  • [ 100-19-6 ]
  • [ 828935-07-5 ]
  • [ 99-81-0 ]
YieldReaction ConditionsOperation in experiment
21% for 1.5 h; Reflux General procedure: Oxone (1.352 g, 2.2 mmol) was added to the well stirred solution of substrate (2 mmol) and NH4Br (0.215 g, 2.2 mmol) in methanol (10 ml) and the reaction mixture was allowed to stir at room temperature (or reflux temperature). After completion of the reaction, as monitored by TLC, the reaction mixture was quenched with aqueous sodium thiosulfate, and extracted with ethyl acetate (3.x.25 ml). Finally, the combined organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and removal of solvent in vacuo yielded a crude residue, which was further purified by column chromatography over silica gel (finer than 200 mesh) to afford pure products. All the products were identified on the basis of 1H NMR and mass spectral data.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 2, p. 191 - 195
  • 6
  • [ 100-12-9 ]
  • [ 99-81-0 ]
  • [ 100-19-6 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 4, p. 784 - 787
  • 7
  • [ 17356-08-0 ]
  • [ 100-19-6 ]
  • [ 99-81-0 ]
Reference: [1] Drug Design, Development and Therapy, 2016, vol. 10, p. 1807 - 1815
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  • [ 100-19-6 ]
  • [ 99-81-0 ]
Reference: [1] Chemische Berichte, 1953, vol. 86, p. 1556,1560
  • 9
  • [ 98-86-2 ]
  • [ 577-59-3 ]
  • [ 100-19-6 ]
  • [ 121-89-1 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 19, p. 2385 - 2389
[2] Tetrahedron Letters, 2001, vol. 42, # 38, p. 6767 - 6769
  • 10
  • [ 98-86-2 ]
  • [ 100-19-6 ]
  • [ 121-89-1 ]
Reference: [1] Catalysis Letters, 2010, vol. 134, # 3-4, p. 270 - 278
  • 11
  • [ 100-19-6 ]
  • [ 13382-61-1 ]
Reference: [1] Patent: WO2016/57834, 2016, A1,
  • 12
  • [ 77287-34-4 ]
  • [ 100-19-6 ]
  • [ 13382-61-1 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1974, vol. 10, p. 1294 - 1297[2] Khimiya Geterotsiklicheskikh Soedinenii, 1974, vol. 10, p. 1472 - 1476
  • 13
  • [ 100-19-6 ]
  • [ 14922-36-2 ]
YieldReaction ConditionsOperation in experiment
79.2% at 110℃; for 1 h; Inert atmosphere SeO2 (0.167 g, 1.5 mmol), p-nitroacetophenone (0.165 g, 1 mmol) in a 25 mL round bottom flask under nitrogen.Add 10 mL of anhydrous pyridine, heat the oil bath to 110 ° C and stir to reflux.After 1 hour, the progress of the reaction was detected by TLC thin layer chromatography, and after cooling for 4 hours, it was cooled to room temperature.Filtration through a Buchner funnel, filtering off the solution containing SeO2 precipitate, washing the residue with 50 mL of ethyl acetate;The filtrate was combined and treated with 1 mmol/L hydrochloric acid (20 mL).The aqueous layer was extracted three times with ethyl acetate (50 mL) to give aqueous layer 2 and organic layer 2;After the organic layer 1 and the organic layer 2 are combined, extracted three times with 25 ml of water to obtain an organic layer 3 and an aqueous layer 3;The aqueous layer 3 was treated with 1 mmol/L NaOH (50 mL), and the reaction solution was diluted to obtainTo the filtrate 4.After the filtrate 4 was combined with the aqueous layer 2, the pH was adjusted to 1.5 with hydrochloric acid (1 mmol/L).The mixture was extracted with EtOAc (3~50 mL).Drying in a vacuum desiccator overnight gave the product 4-nitrophenylglyoxylic acid.Yield: 0.154 g. The yield was 79.2percent.
Reference: [1] Synthetic Communications, 2008, vol. 38, # 24, p. 4434 - 4444
[2] Patent: CN108623611, 2018, A, . Location in patent: Paragraph 0041; 0043; 0044; 0045; 0046
[3] Journal of Organic Chemistry, 2018, vol. 83, # 3, p. 1422 - 1430
[4] Journal of the American Chemical Society, 2010, vol. 132, # 34, p. 11898 - 11899
[5] Chemical Communications, 2013, vol. 49, # 35, p. 3640 - 3642
[6] Organic and Biomolecular Chemistry, 2017, vol. 15, # 20, p. 4320 - 4327
[7] Advanced Synthesis and Catalysis, 2017, vol. 359, # 14, p. 2390 - 2395
[8] Organic Letters, 2017, vol. 19, # 17, p. 4556 - 4559
[9] Advanced Synthesis and Catalysis, 2018, vol. 360, # 17, p. 3345 - 3355
  • 14
  • [ 100-19-6 ]
  • [ 100-27-6 ]
Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 3, p. 438 - 442
[2] Journal of Organic Chemistry, 1984, vol. 49, # 3, p. 438 - 442
  • 15
  • [ 100-19-6 ]
  • [ 19935-81-0 ]
Reference: [1] Patent: US5308848, 1994, A,
  • 16
  • [ 100-12-9 ]
  • [ 19935-81-0 ]
  • [ 90050-69-4 ]
  • [ 100-19-6 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 9, p. 2414 - 2417
  • 17
  • [ 149104-90-5 ]
  • [ 6322-56-1 ]
  • [ 98-86-2 ]
  • [ 100-19-6 ]
  • [ 99-93-4 ]
Reference: [1] Chemical Research in Toxicology, 2011, vol. 24, # 5, p. 687 - 697
  • 18
  • [ 100-19-6 ]
  • [ 58833-57-1 ]
  • [ 5437-38-7 ]
  • [ 100-19-6 ]
Reference: [1] Journal of Physical Chemistry, 1986, vol. 90, # 19, p. 4648 - 4650
  • 19
  • [ 100-19-6 ]
  • [ 64611-67-2 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 2, p. 229 - 231
[2] Synthesis, 2008, # 20, p. 3205 - 3208
[3] Tetrahedron Letters, 1981, vol. 22, # 14, p. 1283 - 1286
[4] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 6, p. 669 - 671
[5] Journal of Organic Chemistry, 1989, vol. 54, # 18, p. 4473 - 4474
[6] Chemische Berichte, 1889, vol. 22, p. 203
[7] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 109, p. 178 - 183
[8] Organic Letters, 2016, vol. 18, # 18, p. 4526 - 4529
[9] European Journal of Organic Chemistry, 2017, vol. 2017, # 30, p. 4434 - 4438
  • 20
  • [ 100-19-6 ]
  • [ 64611-67-2 ]
  • [ 62-23-7 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 41, p. 6065 - 6068
  • 21
  • [ 100-19-6 ]
  • [ 34505-31-2 ]
  • [ 81-20-9 ]
  • [ 100-19-6 ]
Reference: [1] Journal of Physical Chemistry, 1986, vol. 90, # 19, p. 4648 - 4650
  • 22
  • [ 67-56-1 ]
  • [ 100-19-6 ]
  • [ 51513-29-2 ]
  • [ 67395-06-6 ]
  • [ 2345-56-4 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 24, p. 4545 - 4556
  • 23
  • [ 100-19-6 ]
  • [ 4996-22-9 ]
YieldReaction ConditionsOperation in experiment
52% for 36 h; Reflux General procedure: A mixture of a substrate (0.6 mmol), vinyl bromide 2a (0.06 mmol) in DMSO (1.1 mL) was heated in an open flask (the temperature of an oil bath and the reaction time are specified in refPreviewPlaceHolderTable 2). After the completion of the reaction (checked by TLC), the reaction mixture was diluted with water (11 mL), saturated with NaCl and extracted with ethyl acetate (5.x.4 mL). Only in the case of the synthesis of arylglyoxals the organic layer was additionally washed with Na2CO3 (0.12 mmol in 2 mL of water), with saturated aq NaCl and dried with anhydrous Na2SO4. Column chromatography (eluent: gradient petrolether/ethyl acetate) of the extract gave the pure products.
Reference: [1] Tetrahedron Asymmetry, 2010, vol. 21, # 18, p. 2244 - 2248
[2] Tetrahedron, 2011, vol. 67, # 41, p. 8000 - 8008
[3] Journal of Fluorine Chemistry, 2010, vol. 131, # 12, p. 1289 - 1296
[4] Tetrahedron Letters, 2011, vol. 52, # 31, p. 4036 - 4038
[5] Tetrahedron, 2013, vol. 69, # 1, p. 22 - 28
[6] Synlett, 2013, vol. 24, # 8, p. 998 - 1000
[7] Tetrahedron, 2017, vol. 73, # 47, p. 6587 - 6596
[8] Journal of Organometallic Chemistry, 2013, vol. 744, p. 101 - 107
[9] Journal of Sulfur Chemistry, 2013, vol. 34, # 5, p. 464 - 473
[10] Journal of the American Chemical Society, 2013, vol. 135, # 45, p. 16849 - 16852
[11] Journal of Fluorine Chemistry, 2014, vol. 168, p. 151 - 157
[12] Tetrahedron Letters, 2015, vol. 56, # 32, p. 4701 - 4703
[13] Turkish Journal of Chemistry, 2015, vol. 39, # 2, p. 244 - 254
[14] Research on Chemical Intermediates, 2015, vol. 41, # 10, p. 7263 - 7272
[15] Australian Journal of Chemistry, 2015, vol. 68, # 10, p. 1529 - 1534
[16] Journal of Organic Chemistry, 2016, vol. 81, # 15, p. 6402 - 6408
[17] Journal of the Iranian Chemical Society, 2017, vol. 14, # 11, p. 2299 - 2304
[18] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 6, p. 3163 - 3168
[19] Heterocyclic Communications, 2018, vol. 24, # 1, p. 37 - 41
[20] Tetrahedron Letters, 2018, vol. 59, # 31, p. 2970 - 2974
[21] Organic and Biomolecular Chemistry, 2018, vol. 16, # 38, p. 6998 - 7003
[22] Heterocyclic Communications, 2018, vol. 24, # 6, p. 297 - 302
  • 24
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  • [ 90434-58-5 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1963, vol. 72, p. 202 - 207
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  • [ 23600-83-1 ]
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  • [ 23600-83-1 ]
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  • [ 5425-81-0 ]
Reference: [1] Patent: WO2011/55289, 2011, A2,
[2] Patent: WO2012/29032, 2012, A2,
[3] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 324 - 342
[4] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 337 - 347
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[2] Journal of Physical Chemistry B, 2005, vol. 109, # 2, p. 724 - 730
[3] Tetrahedron Letters, 2008, vol. 49, # 33, p. 4918 - 4921
[4] Angewandte Chemie - International Edition, 2015, vol. 54, # 30, p. 8658 - 8661[5] Angew. Chem., 2015, vol. 127, # 30, p. 8782 - 8785,4
[6] Tetrahedron Letters, 2018, vol. 59, # 11, p. 1023 - 1027
[7] Journal of the American Chemical Society, 2018,
  • 29
  • [ 100-19-6 ]
  • [ 189083-63-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 14, p. 4138 - 4140
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