Home Cart 0 Sign in  
X

[ CAS No. 150-19-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
3d Animation Molecule Structure of 150-19-6
Chemical Structure| 150-19-6
Chemical Structure| 150-19-6
Structure of 150-19-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 150-19-6 ]

Related Doc. of [ 150-19-6 ]

Alternatived Products of [ 150-19-6 ]
Product Citations

Product Citations

Canale, Vittorio ; Czekajewska, Joanna ; Klesiewicz, Karolina , et al. DOI: PubMed ID:

Abstract: The alarming increase in the resistance of bacteria to the currently available antibiotics necessitates the development of new effective antimicrobial agents that are active against bacterial pathogens causing major public health problems. For this purpose, our inhouse libraries were screened against a wide panel of clin. relevant Gram-pos. and Gram-neg. bacteria, based on which compound I was selected for further optimization. Synthetic efforts in a group of arylurea derivatives of aryloxy(1-phenylpropyl) alicyclic diamines, followed with an in vitro evaluation of the activity against multidrug-resistant strains identified compound 44 (1-(3-chlorophenyl)-3-(1-{3-phenyl-3-[3-(trifluoromethyl)phenoxy] propyl}piperidin-4-yl)urea). Compound 44 showed antibacterial activity against Gram-pos. bacteria including fatal drug-resistant strains i.e., Staphylococcus aureus (methicillin-resistant, MRSA; vancomycin-intermediate, VISA) and Enterococcus faecium (vancomycin-resistant, VREfm) at low concentrations (0.78-3.125 μg/mL) comparable to last resort antibiotics (i.e., vancomycin and linezolid). It is also potent against biofilm-forming S. aureus and Staphylococcus epidermidis (including linezolid-resistant, LRSE) strains, but with no activity against Gram-neg. bacteria (Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa). Compound 44 showed strong bactericidal properties against susceptible and drug-resistant Gram-pos. bacteria. Depolarization of the bacterial cytoplasmic membrane induced by compound 44 suggests a dissipation of the bacterial membrane potential as its mechanism of antibacterial action. The high antimicrobial activity of compound 44, along with its selectivity over mammalian cells (lung MCR-5 and skin BJ fibroblast cell lines) and no hemolytic properties toward horse erythrocytes, proposes arylurea derivatives of aryloxy(1-phenylpropyl) alicyclic diamines for development of novel antibacterial agents.

Keywords: Arylurea derivatives ; Antibacterial properties ; Anti-MRSA activity ; Anti-VRE activity ; Anti-LRSE activity ; Depolarization of bacterial cell membrane

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ;

Product Details of [ 150-19-6 ]

CAS No. :150-19-6 MDL No. :MFCD00002267
Formula : C7H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ASHGTJPOSUFTGB-UHFFFAOYSA-N
M.W : 124.14 Pubchem ID :9007
Synonyms :
Chemical Name :m-Methoxyphenol

Calculated chemistry of [ 150-19-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 34.96
TPSA : 29.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.55
Log Po/w (XLOGP3) : 1.34
Log Po/w (WLOGP) : 1.4
Log Po/w (MLOGP) : 1.15
Log Po/w (SILICOS-IT) : 1.36
Consensus Log Po/w : 1.36

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.88
Solubility : 1.63 mg/ml ; 0.0131 mol/l
Class : Very soluble
Log S (Ali) : -1.56
Solubility : 3.42 mg/ml ; 0.0275 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.91
Solubility : 1.54 mg/ml ; 0.0124 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.02

Safety of [ 150-19-6 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338+P310 UN#:2810
Hazard Statements:H302+H332-H311-H315-H318 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 150-19-6 ]

* 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 [ 150-19-6 ]
  • Downstream synthetic route of [ 150-19-6 ]

[ 150-19-6 ] Synthesis Path-Upstream   1~48

  • 1
  • [ 150-19-6 ]
  • [ 42327-52-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 14, p. 4053 - 4056
[2] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 8, p. 2545 - 2551
[3] Synthetic Communications, 1996, vol. 26, # 6, p. 1233 - 1245
[4] Synthetic Communications, 1996, vol. 26, # 6, p. 1233 - 1245
[5] Tetrahedron, 1989, vol. 45, # 18, p. 5895 - 5906
[6] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. <B> 19, # 6, p. 500 - 503
[7] Proceedings of the Chemical Society, London, 1912, vol. 28, p. 7
[8] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1911, vol. 43, p. 1188[9] Chem. Zentralbl., 1912, vol. 83, # I, p. 1022
[10] Journal of the Chemical Society, 1926, p. 943,946[11] Journal of the Chemical Society, 1927, p. 2095,2098
[12] Chemische Berichte, 1924, vol. 57, p. 210
[13] Proceedings of the Chemical Society, London, 1912, vol. 28, p. 7
[14] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1911, vol. 43, p. 1188[15] Chem. Zentralbl., 1912, vol. 83, # I, p. 1022
[16] Journal of the Chemical Society, 1926, p. 943,946[17] Journal of the Chemical Society, 1927, p. 2095,2098
[18] Journal of the Chemical Society, 1950, p. 2272,2275
[19] Chemistry - An Asian Journal, 2016, vol. 11, # 5, p. 757 - 765
  • 2
  • [ 41580-72-7 ]
  • [ 150-19-6 ]
  • [ 42327-52-6 ]
Reference: [1] Chemistry - An Asian Journal, 2016, vol. 11, # 5, p. 757 - 765
  • 3
  • [ 150-19-6 ]
  • [ 50551-63-8 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1900, vol. 312, p. 332
[2] Organic Letters, 2016, vol. 18, # 21, p. 5624 - 5627
[3] European Journal of Organic Chemistry, 2018, vol. 2018, # 22, p. 2774 - 2779
  • 4
  • [ 150-19-6 ]
  • [ 50551-63-8 ]
  • [ 18014-96-5 ]
Reference: [1] Tetrahedron, 2015, vol. 71, # 29, p. 4835 - 4841
  • 5
  • [ 150-19-6 ]
  • [ 23681-89-2 ]
Reference: [1] Patent: WO2017/218960, 2017, A1,
  • 6
  • [ 150-19-6 ]
  • [ 107-14-2 ]
  • [ 15832-09-4 ]
YieldReaction ConditionsOperation in experiment
54.8% With hydrogenchloride; sodium hydroxide In 1,4-dioxane; water EXAMPLE 5
Preparation of 6-methoxy-3-benzofuranone
Chloroacetonitrile (3.5 ml, 55.2 mmol) was added dropwise to a stirred solution containing 3-methoxyphenol (5 ml, 46 mmol) and zinc chloride (6.9 g, 50.6 mmol) in anhydrous dioxane (30 ml) at room temperature.
The resulting solution was saturated with dry hydrogen chloride gas.
After stirring at room temperature overnight, the yellow precipitate was filtered and washed with anhydrous ether (100 ml).
The collected precipitate was dissolved in water (80 ml) and heated to reflux for 1 hour.
The solution was allowed to cool to approximately 40° C., and aqueous sodium hydroxide (20percent w/v) (7.5 ml) was added.
After stirring at that temperature for 30 minutes a pale yellow precipitate had formed.
A heterogeneous system was then taken to pH.approx.7 by addition of hydrochloric acid (1 M).
The precipitate was filtered, washed with water, and recrystallized from acetone to give the desired compound as a light yellow powder (4.14 g, 54.8percent).
1H NMR: 8 (ppm): 3.85 (OMe); 4.9 (CH2); 6.50-6.46 (2 H-Phenyl); 7.70-7.66 (1 H-Phenyl).
Reference: [1] Patent: US6307070, 2001, B1,
  • 7
  • [ 150-19-6 ]
  • [ 98232-51-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 23, p. 5025 - 5033
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5436 - 5441
[3] Patent: WO2012/50848, 2012, A1,
  • 8
  • [ 150-19-6 ]
  • [ 105-50-0 ]
  • [ 62935-72-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 6, p. 1094 - 1099
  • 9
  • [ 150-19-6 ]
  • [ 77-92-9 ]
  • [ 62935-72-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 32, p. 7777 - 7791
[2] Journal of the American Chemical Society, 1950, vol. 72, p. 3987,3989
[3] Synthetic Communications, 2015, vol. 45, # 17, p. 2043 - 2052
  • 10
  • [ 150-19-6 ]
  • [ 62935-72-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 25, p. 6349 - 6362
  • 11
  • [ 150-19-6 ]
  • [ 542-05-2 ]
  • [ 62935-72-2 ]
Reference: [1] Journal of the Chemical Society, 1915, vol. 107, p. 1637
[2] Synlett, 2012, vol. 23, # 15, p. 2189 - 2194
[3] Tetrahedron Letters, 2014, vol. 55, # 15, p. 2362 - 2365
  • 12
  • [ 123-39-7 ]
  • [ 217813-03-1 ]
  • [ 150-19-6 ]
  • [ 148-53-8 ]
YieldReaction ConditionsOperation in experiment
4%
Stage #1: With tetrabutyl ammonium fluoride In acetonitrile at 20℃; for 3 h; Inert atmosphere
Stage #2: at 20℃;
General procedure: To a solution of 3-methoxy-2-(trimethylsilyl)phenyl triflate 1 (53 μL, 0.20 mmol) and 1-formylpiperidine 4, N,N-dibenzylformamide 6, or N-methylformamide 8 (2.0 mmol) in CH3CN (1.4 mL) was added TBAF (1.0 M solution in CH3CN, 0.60 mL, 0.60 mmol) under argon atmosphere at room temperature. After being stirred at the same temperature for 3 h, H2O (0.1 mL) was added to the reaction mixture. The reaction mixture was concentrated under reduced pressure. Purification of the residue by flash silica gel column chromatography (AcOEt/hexane=1/20 to 1/8 with 2percent CH2Cl2) afforded the products 2, 5, 7, and 9.
Reference: [1] Tetrahedron, 2012, vol. 68, # 1, p. 179 - 189
  • 13
  • [ 150-19-6 ]
  • [ 13895-38-0 ]
Reference: [1] Synthetic Communications, 1993, vol. 23, # 3, p. 343 - 348
[2] Organic and Biomolecular Chemistry, 2007, vol. 5, # 3, p. 531 - 546
[3] Chemische Berichte, 1902, vol. 35, p. 1480
[4] Bulletin de la Societe Chimique de France, 1972, p. 4061 - 4067
[5] Journal fuer Praktische Chemie/Chemiker-Zeitung, 1993, vol. 335, # 1, p. 103 - 104
[6] Scientia Pharmaceutica, 2005, vol. 73, # 3, p. 95 - 100
  • 14
  • [ 150-19-6 ]
  • [ 39501-58-1 ]
  • [ 13895-38-0 ]
Reference: [1] Patent: US5250741, 1993, A,
  • 15
  • [ 150-19-6 ]
  • [ 13895-38-0 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 8, p. 2774 - 2779
[2] Journal of Organic Chemistry, 1996, vol. 61, # 8, p. 2774 - 2779
[3] Journal of Organic Chemistry, 1996, vol. 61, # 8, p. 2774 - 2779
  • 16
  • [ 150-19-6 ]
  • [ 39501-58-1 ]
  • [ 13895-38-0 ]
Reference: [1] Synthetic Communications, 1995, vol. 25, # 15, p. 2327 - 2335
  • 17
  • [ 150-19-6 ]
  • [ 17302-49-7 ]
  • [ 13895-38-0 ]
Reference: [1] Chemische Berichte, 1902, vol. 35, p. 1480
  • 18
  • [ 150-19-6 ]
  • [ 98910-61-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1985, vol. 22, # 2, p. 363 - 368
  • 19
  • [ 150-19-6 ]
  • [ 703-23-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 34, p. 9026 - 9029[2] Angew. Chem., 2014, vol. 126, # 34, p. 9172 - 9175,4
  • 20
  • [ 150-19-6 ]
  • [ 63604-94-4 ]
YieldReaction ConditionsOperation in experiment
79% With N-Bromosuccinimide In dichloromethane at 20℃; for 1 h; Inert atmosphere 3-methoxyphenol (10, 1.034 g, 96 percent, 8.0 mmol) was dissolved in DCM (160 mL) and N-bromosuccinimide (1.424 g, 8.0 mmol) was added slowly at maximum stirring rate. The solution was stirred at ambient temperature for 1 h and quenched with water. The inorganic layer was extracted twice with DCM, and the combined organic layers were dried over MgSO4. The solvents were removed in vacuo, and the residue was purified by flash chromatography (DCM/isohexane 2:1) to afford phenol 6 (1.290 g, 79 percent) as a white solid.
64% With N-Bromosuccinimide In dichloromethane at 0 - 20℃; for 2 h; Inert atmosphere To the solution of 33 A (9.8 g, 79 mmol, 1.0 eq) in DCM (100 mL) was added NBS (14.8 g, 82.9 mmol, 1.05 eq) in DCM (150 mL) dropwise at 0 °C. The reaction mixture was stirred at room temperature for 2 hours under nitrogen atmosphere before it was concentrated in vacuo to dryness. The residue was purified by flash chromatography on silica (PE EA = 20: 1 to 5: 1) to give 33B (10.2 g, 64percent).
63% With bromine; silver trifluoroacetate In chloroform at 20℃; for 20 h; Step B - Synthesis of Compound Int-22b; To a suspension of 3-methoxyphenol (3.0 g, 24.18 mmol) and CF3COOAg (5.3 g, 24.2 mmol) in CHCI3 ( 1 5 mL) was added Br in CHCI3 (20 mL) dropwise and the mixture was allowed to stir at room temperature for 20 hours. The reaction was quenched with aqueous NaS03 and washed with water. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue that was purified using flash chromatography on silica gel to provide compound Int-22b (3.1 g, 63percent). NMR: (CDC13) δ: 3.77 (s, 3 H), 5.47 (s, 1 H), 6.40-6.42 (m, 1 H), 6.60 (s, 1 H), 7.30-7.32 (m, 1 H).
63% With bromine; silver trifluoroacetate In chloroform at 20℃; for 20 h; Synthesis of Compound Int-22bInt 22bTo a suspension of 3-methoxyphenol (3.0 g, 24.18 mmol) and CF3COOAg (5.3 g, 24.2 mmol) in CHC13 (15 mL) was added Br2 in CHC13 (20 mL) dropwise and the mixture was allowed to stir at room temperature for 20 hours. The reaction was quenched with aqueous NaS03 and washed with water. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue that was purified using flash chromatography on silica gel to provide compound Int-22b (3.1 g, 63percent). 1H MR: (CDC13) δ: 3.77 (s, 3 H), 5.47 (s, 1 H), 6.40-6.42 (m, 1 H), 6.60 (s, 1 H), 7.30-7.32 (m, 1 H).

Reference: [1] Synthetic Communications, 2007, vol. 37, # 2, p. 323 - 328
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 11, p. 2470 - 2481
[3] Journal of the Serbian Chemical Society, 2011, vol. 76, # 5, p. 685 - 692
[4] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 22, p. 6175 - 6177
[5] Journal of Medicinal Chemistry, 2002, vol. 45, # 18, p. 3972 - 3983
[6] Angewandte Chemie - International Edition, 2012, vol. 51, # 12, p. 2925 - 2929
[7] Journal of Organic Chemistry, 2016, vol. 81, # 20, p. 9765 - 9774
[8] Patent: WO2016/149393, 2016, A1, . Location in patent: Paragraph 0326
[9] Patent: WO2012/125926, 2012, A2, . Location in patent: Page/Page column 80
[10] Patent: WO2012/122716, 2012, A1, . Location in patent: Page/Page column 99
[11] Chemical Communications, 2018, vol. 54, # 39, p. 4935 - 4938
[12] Angewandte Chemie - International Edition, 2007, vol. 46, # 9, p. 1448 - 1450
[13] Dalton Transactions, 2013, vol. 42, # 12, p. 4218 - 4222
[14] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 12, p. 2927 - 2932
[15] Journal of the Chemical Society, Chemical Communications, 1980, # 22, p. 1103 - 1104
[16] Organic Letters, 2003, vol. 5, # 20, p. 3679 - 3682
[17] Patent: US6365602, 2002, B1,
[18] Patent: WO2010/145203, 2010, A1, . Location in patent: Page/Page column 43-44
[19] Patent: WO2017/218960, 2017, A1, . Location in patent: Paragraph 00389
  • 21
  • [ 150-19-6 ]
  • [ 63604-94-4 ]
  • [ 102127-34-4 ]
YieldReaction ConditionsOperation in experiment
28% With N-Bromosuccinimide In acetonitrile at 0℃; for 3 h; A solution of 40.0 gm (322.2 mMol) 3-methoxyphenol in 1 L acetonitrile was cooled to 0° C. under a nitrogen atmosphere. To this cooled solution was added a solution of 57.35 gm (322.2 mMol) N-bromosuccinimide in 500 mL acetonitrile dropwise at a rate to maintain the temperature of the reaction mixture at 0° C. (approximately 2 hours). The reaction mixture was stirred at 0° C. for about 1 hour after the addition was complete and was then concentrated under reduced pressure. The residue was treated with carbon tetrachloride and the solid which formed was removed by filtration. The filtrate was concentrated under reduced pressure to provide a mixture of bromination isomers as a red oil.This oil was subjected to silica gel chromatography, eluting with a gradient system of hexane containing from 0-30percent ethyl acetate. Fractions containing the fastest eluting compound were combined and concentrated under reduced pressure to provide 18.1 gm (28percent) of 2-bromo-5-methoxyphenol as a clear liquid.1H-NMR(CDCl3): δ 7.31 (d, 1H), 6.6 (d, 1H), 6.41 (dd, 1H), 5.5 (s, 1H), 3.77 (s, 3H).Fractions containing the later eluting components were combined and concentrated under reduced pressure. This residue was subjected to silica gel chromatography, eluting with dichloromethane. Fractions containing substantially pure 4-bromo-5-methoxyphenol were combined and concentrated under reduced pressure to provide 24.1 gm (37percent) of a white crystalline solid (m.p.=68-69° C.).1H-NMR(CDCl3): δ 7.34 (d, 1H), 6.45 (d, 1H), 6.33 (dd, 1H), 4.9 (br s, 1H), 3.85 (s, 3H).
28% With N-Bromosuccinimide In acetonitrile at 0℃; for 3 h; A solution of 40.0 gm (322.2 mMol) 3-methoxyphenol in 1L acetonitrile was cooled to 0°C under a nitrogen atmosphere. To this cooled solution was added a solution of 57.35 gm (322.2 mMol) N-bromosuccinimide in 500 mL acetonitrile dropwise at a rate to maintain the temperature of the reaction mixture at 0°C (approximately 2 hours). The reaction mixture was stirred at 0°C for about 1 hour after the addition was complete and was then concentrated under reduced pressure. The residue was treated with carbon tetrachloride and the solid which formed was removed by filtration. The filtrate was concentrated under reduced pressure to provide a mixture of bromination isomers as a red oil. This oil was subjected to silica gel chromatography, eluting with a gradient system of hexane containing from 0-30percent ethyl acetate. Fractions containing the fastest eluting compound were combined and concentrated under reduced pressure to provide 18.1 gm (28percent) of 2-bromo-5-methoxyphenol as a clear liquid.1H-NMR(CDCl3): δ 7.31 (d, 1H), 6.6 (d, 1H), 6.41 (dd, 1H), 5.5 (s, 1H), 3.77 (s, 3H). Fractions containing the later eluting components were combined and concentrated under reduced pressure. This residue was subjected to silica gel chromatography, eluting with dichloromethane. Fractions containing substantially pure 4-bromo-5-methoxyphenol were combined and concentrated under reduced pressure to provide 24.1 gm (37percent) of a white crystalline solid (m.p. = 68-69°C).1H-NMR(CDCl3): δ 7.34 (d, 1H), 6.45 (d, 1H), 6.33 (dd, 1H), 4.9 (br s, 1H), 3.85 (s, 3H).
Reference: [1] Synlett, 1997, vol. 1997, # 11, p. 1241 - 1242
[2] Synlett, 1997, vol. 1997, # 11, p. 1241 - 1242
[3] Patent: US7045545, 2006, B1, . Location in patent: Page/Page column 19
[4] Patent: EP1204659, 2003, B1, . Location in patent: Page/Page column 14
[5] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 622 - 627
  • 22
  • [ 150-19-6 ]
  • [ 63604-94-4 ]
YieldReaction ConditionsOperation in experiment
85% With bromine In water (1)
To a mixed solution of 25 g of 3-methoxyphenol and 100 ml of carbon disulfide (CS2) was added dropwise 10.3 ml of bromine at room temperature.
After stirring the mixture for 30 minutes, the solvent was removed under reduced pressure, and water was added to the residue.
The reaction mixture was extracted with diethyl ether.
The extract was washed and dried, and the solvent was removed under reduced pressure to give 34.8 g of 2-bromo-5-methoxyphenol (yield: 85percent, boiling point: 96°-98° C. (4 mmHg), colorless oily product).
Reference: [1] Patent: US5849732, 1998, A,
  • 23
  • [ 150-19-6 ]
  • [ 63604-94-4 ]
  • [ 66693-87-6 ]
Reference: [1] Organic Process Research and Development, 2004, vol. 8, # 1, p. 33 - 44
  • 24
  • [ 556-64-9 ]
  • [ 150-19-6 ]
  • [ 39835-11-5 ]
Reference: [1] Synthetic Communications, 1990, vol. 20, # 1, p. 71 - 84
  • 25
  • [ 150-19-6 ]
  • [ 98-85-1 ]
  • [ 85-27-8 ]
  • [ 106552-08-3 ]
Reference: [1] Synlett, 2011, # 11, p. 1585 - 1591
  • 26
  • [ 150-19-6 ]
  • [ 2612-02-4 ]
Reference: [1] Synthesis, 1984, vol. NO. 9, p. 758 - 760
  • 27
  • [ 150-19-6 ]
  • [ 16292-95-8 ]
YieldReaction ConditionsOperation in experiment
75% With copper(II) nitrate trihydrate In tetrahydrofuran at 50℃; for 1 h; General procedure: A suspension of 2-methylphenol(18.5 mmol, 1.0 eq) and Cu(NO3)2.3H2O (27.7 mmol, 1.5 eq) in THF was stirred magnetically at 60°C or reflux for several hours. Then after the solvent was removed under vacuum, the mixture was extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine (5mL), dried over anhydrous MgSO4 and concentrated under vacuum. The crude residue was purified by column chromatography to afford the product (67-90percent).
35.23% at 0℃; for 3 h; Concentrated nitric acid (55.83 mg, 886.09 mmol) was added to a solution of trimethoxyphenol (100 mg, 805.54mmol) in acetic acid (2 mL) and stirred at 0 °C for 3 hours. The aqueous phase was extracted with ethyl acetate (20 mL* 2). The combined organic layers were washed with NaCl solution (20 mL * 2), and then dried over sodium sulfate,filtered and evaporated, and the residue was purified by column chromatography to give compound 72A (48 mg, 35.23percent).1H NMR (400MHz, METHANOL-d4) = 10.914 (s, 1H), 7.901 - 7.887(d, 1H), 6.614-6.609 (d, 1H), 6.50- 6.48 (m, 1H),3.875 (s, 3H)
Reference: [1] Arkivoc, 2014, vol. 2014, # 5, p. 64 - 71
[2] Patent: EP3293177, 2018, A1, . Location in patent: Paragraph 0211; 0212
[3] Bulletin de la Societe Chimique de France, 1972, p. 4061 - 4067
[4] Synthetic Communications, 2007, vol. 37, # 16, p. 2771 - 2776
  • 28
  • [ 150-19-6 ]
  • [ 3114-61-2 ]
  • [ 16292-95-8 ]
  • [ 704-14-3 ]
YieldReaction ConditionsOperation in experiment
29% With bismuth (III) nitrate pentahydrate In acetone at 0℃; for 20 h; General procedure: To a solid mixture of phenol (1–3 equiv) and Bi(NO3)35H2O (1 equiv) or Fe(NO3)39H2O (1 equiv) was added acetone (10 ml/mmol). The resulting mixture was stirred at room temperature under air or at reflux for 2–24 hours, Tables 1 and 2. When the reaction was completed the insoluble materials were filtered off using a pad of Celite and the residue was washed by acetone (ca. 5 ml/mmol). The filtrate was treated by NaHCO3 (0.1 g/mmol) until evolution of CO2 stopped. Insoluble material was filtered off again, and the solvent was removed under vacuum in a water bath 25–35°C. The nitrated products were separated or purified using silica gel chromatography, to give pure phenolic compounds. All products were characterized by 1H NMR,13C NMR and IR and were identified by comparison of the spectral data and melting points with those reported in literature and characterized.
Reference: [1] Synthetic Communications, 2015, vol. 45, # 1, p. 143 - 150
  • 29
  • [ 150-19-6 ]
  • [ 16292-95-8 ]
  • [ 704-14-3 ]
Reference: [1] Journal of the Chemical Society, 1929, p. 2778
[2] Monatshefte fuer Chemie, 1880, vol. 1, p. 887[3] Monatshefte fuer Chemie, 1881, vol. 2, p. 369 Anm. 3
  • 30
  • [ 150-19-6 ]
  • [ 60-29-7 ]
  • [ 7697-37-2 ]
  • [ 7782-77-6 ]
  • [ 16292-95-8 ]
  • [ 704-14-3 ]
Reference: [1] Monatshefte fuer Chemie, 1880, vol. 1, p. 887[2] Monatshefte fuer Chemie, 1881, vol. 2, p. 369 Anm. 3
  • 31
  • [ 150-19-6 ]
  • [ 704-14-3 ]
YieldReaction ConditionsOperation in experiment
55%
Stage #1: With propionic acid; sodium nitrite In water at -5℃; for 1 h;
Stage #2: With nitric acid In water at -5 - 20℃; for 16 h;
Benzoxazole Formation Procedures:
Compound 3:
A solution of 3-methoxyphenol (10 g, 80.55 mmol) in propionic acid (80 mL) was treated at -5° C. with a solution of NaNO2 (5.61 g, 81.30 mmol) in water (13 mL).
After stirring for 1 h at -5° C., nitric acid (6.7 mL, 161.10 mmol) was added.
The slurry was stirred for 1 h at -5° C., and then at room temperature for 16 h.
Water (80 mL) was then added in a dropwise fashion at room temperature.
The resultant solid was filtered, washed with 50percent aqueous propionic acid, and dried to give 7.47 g (55percent) of 5-methoxy-2-nitro-phenol.
36% at 20℃; for 0.5 h; Inert atmosphere To a solution of3-methoxyphenol (6.0 g, 48.33 mmol) in AcOH (70 ml) was added HNO3 (60percent,5.08 g, 48.33 mmol) at 0 °C under nitrogenatmosphere and the mixture was stirred at RT for 30 min. The aqueous layer wasfurther extracted with EtOAc, and the combined organic solutions were driedover MgSO4, filtered and concentrated in vacuo. The residuewas purified by flash column chromatography (n-hexane:EtOAc = 20:1) toafford the 1a (2.84 g, 17.40 mmol,36percent) as an orange solid: Rf = 0.9 (n-hexane:EtOAc =3:1); 1H NMR (400 MHz, CDCl3) δ 11.05 (1H, s), 8.04 (1H,d, J = 8.0 Hz), 6.53 (1H, d, J= 2.4 Hz), 6.52 (1H,dd, J = 2.4, 8.0Hz), 3.89 (3H, s); 13C NMR (100 MHz, CDCl3) δ 166.9, 157.8,127.5, 126.8, 109.3, 101.2, 56.0.
Reference: [1] Tetrahedron, 1998, vol. 54, # 27, p. 7843 - 7848
[2] Patent: US2011/224269, 2011, A1, . Location in patent: Page/Page column 20
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 3067 - 3072
[4] Journal of the Chemical Society, 1935, p. 946
[5] Yakugaku Zasshi, 1959, vol. 78, p. 931[6] Chem.Abstr., 1960, p. 497
[7] Bulletin de la Societe Chimique de France, 1972, p. 4061 - 4067
[8] Journal of Organic Chemistry, 1991, vol. 56, # 5, p. 1788 - 1800
[9] Phytochemistry, 1994, vol. 37, # 2, p. 297 - 300
[10] Scientia Pharmaceutica, 2005, vol. 73, # 3, p. 95 - 100
[11] Journal fuer Praktische Chemie/Chemiker-Zeitung, 1993, vol. 335, # 1, p. 103 - 104
[12] Synthetic Communications, 1993, vol. 23, # 3, p. 343 - 348
[13] Patent: US2003/216582, 2003, A1, . Location in patent: Page/Page column 4
  • 32
  • [ 150-19-6 ]
  • [ 3114-61-2 ]
  • [ 16292-95-8 ]
  • [ 704-14-3 ]
YieldReaction ConditionsOperation in experiment
29% With bismuth (III) nitrate pentahydrate In acetone at 0℃; for 20 h; General procedure: To a solid mixture of phenol (1–3 equiv) and Bi(NO3)35H2O (1 equiv) or Fe(NO3)39H2O (1 equiv) was added acetone (10 ml/mmol). The resulting mixture was stirred at room temperature under air or at reflux for 2–24 hours, Tables 1 and 2. When the reaction was completed the insoluble materials were filtered off using a pad of Celite and the residue was washed by acetone (ca. 5 ml/mmol). The filtrate was treated by NaHCO3 (0.1 g/mmol) until evolution of CO2 stopped. Insoluble material was filtered off again, and the solvent was removed under vacuum in a water bath 25–35°C. The nitrated products were separated or purified using silica gel chromatography, to give pure phenolic compounds. All products were characterized by 1H NMR,13C NMR and IR and were identified by comparison of the spectral data and melting points with those reported in literature and characterized.
Reference: [1] Synthetic Communications, 2015, vol. 45, # 1, p. 143 - 150
  • 33
  • [ 150-19-6 ]
  • [ 16292-95-8 ]
  • [ 704-14-3 ]
Reference: [1] Journal of the Chemical Society, 1929, p. 2778
[2] Monatshefte fuer Chemie, 1880, vol. 1, p. 887[3] Monatshefte fuer Chemie, 1881, vol. 2, p. 369 Anm. 3
  • 34
  • [ 150-19-6 ]
  • [ 7664-93-9 ]
  • [ 64-19-7 ]
  • [ 704-14-3 ]
Reference: [1] Journal of the Chemical Society, 1935, p. 946
  • 35
  • [ 150-19-6 ]
  • [ 60-29-7 ]
  • [ 7697-37-2 ]
  • [ 7782-77-6 ]
  • [ 16292-95-8 ]
  • [ 704-14-3 ]
Reference: [1] Monatshefte fuer Chemie, 1880, vol. 1, p. 887[2] Monatshefte fuer Chemie, 1881, vol. 2, p. 369 Anm. 3
  • 36
  • [ 67-56-1 ]
  • [ 150-19-6 ]
  • [ 20734-74-1 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 17, p. 7325 - 7328
  • 37
  • [ 616-38-6 ]
  • [ 108-46-3 ]
  • [ 150-19-6 ]
  • [ 496-73-1 ]
  • [ 20734-74-1 ]
  • [ 151-10-0 ]
Reference: [1] Journal of Catalysis, 2006, vol. 243, # 2, p. 376 - 388
  • 38
  • [ 150-19-6 ]
  • [ 41046-70-2 ]
YieldReaction ConditionsOperation in experiment
74% With iodine; silver trifluoroacetate In chloroform at 20℃; for 62 h; Add a fine suspension of iodine (25.4 g, 100 mmol) in CHCl3 (700 mL) dropwise to a stirred mixture of 3-methoxyphenol (10.8 mL, 100 mmol), silver trifluoroacetate (22.1 g, 100 mmol), and CHC13 (100 mL) over 2h under N2 at room temperature. Stir at room temperature under N2 for 60h then filter mixture over Celite0 and rinse pad with CHCL3. WASH solution with aqueous 0.1 N NA2S204 solution, saturated NAHCO3 solution and backextract from aqueous with CHCl3. Dry combined organic layers over NA2SO4 and concentrate to get 26.6 g brown oil. Purify the residue by flash chromatography on silica gel eluting with CHCl3 to afford 2-iodo-5-methoxy-phenol (18.4 g, 74percent). MS (IS) 249 (M-1)-. Add copper (1) iodide (0.28 g, 1.5 mmol) to a stirred solution of 2-iodo-5- methoxy-phenol (18.4 g, 73.6 mmol) and trimethylsilyl acetylene (15.6 mL, 110.4 mmol) in THF (225 mL, anhydrous) in a dry RB flask. Add dichlorobis (triphenylphosphine) palladium (II) (1.55 g, 2.2 mmol) and diisopropylamine (21.7 mL, 154.5 mmol) and stir the mixture at room temperature under N2 overnight Quench reaction with water and extract with EtOAc (x3). Dry combined organic layers over MGS04 and concentrate to get 29 g black oil. Adsorb on SI02 and purify the residue by flash chromatography on silica gel eluting with 0-15percent EtOAc/hexanes to afford 5-methoxy-2- trimethylsilanylethynyl-phenol (11.5 g, 71percent). MS (IS) 221 (M+1) +. Add diisopropylamine (11.0 mL, 78.3 mmol) to a rapidly stirred solution OF 5- methoxy-2-trimethylsilanylethynyl-phenol (11.5 g, 52. 2 mmol) in CHZCLZ at room temperature under N2. Add 2- (trimethylsilyl) ethoxymethyl chloride (13.9 mL, 78.3 mmol) dropwise over 5 minutes and stir at room temperature under N2 overnight Acidify with aqueous 1N HCl solution, add water, separate layers. Extract from aqueous layer with CH2C12 (x2), dry combined organic layers over MgS04 and concentrate. Adsorb on SI02 and purify the residue by flash chromatography on silica gel eluting with 0-5percent ETOAC/HEXANES to afford 4-methoxy-2- (2-trimethylsilanyl-ethoxymethoxy)-l- trimethylsilanylethynyl-benzene (13.5 g, 74percent). MS (IS) 351 (M+1) . Add a solution of potassium hydroxide (2.3 g, 40.4 mmol) in water (20 ML) dropwise to a rapidly stirred solution of 4-METHOXY-2- (2-TRIMETHYLSILANYL- ETHOXYMETHOXY)-L-TRIMETHYLSILANYLETHYNYL-BENZENE (13.5 g, 38. 5 mmol) in methanol (200 ML) and stir at room temperature for 1 hour. Concentrate, add brine to residue and extract with EtOAc (x2). Dry combined organic layers over MGS04 and concentrate to get 11.7 g brown oil. Adsorb on Si02 and purify the residue by flash chromatography on silica gel eluting with 0-10percent EtOAc/hexanes to afford [2- (2-ethynyl-5-methoxy- PHENOXYMETHOXY)-ETHYL]-TRIMETHYL-SILANE (10.0 g, 93percent). MS (IS) 279 (M+1) +. Add 1,4-phenylenediisocyanate (6.41 g, 40. 0 mmol) to a stirred solution of [2- (2- ETHYNYL-5-METHOXY-PHENOXYMETHOXY)-ETHYL]-TRIMETHYL-SILANE (5.57 g, 20.0 mmol) and 6- nitro-hexanoic acid ethyl ester (7.56 g, 40.0 mmol) in toluene (150 mL, anhydrous) and stir under N2. Add triethylamine (5.6 ML, 40.0 mmol) and heat to reflux under N2. After 2 hours add additional toluene (150 mL, anhydrous) and continue refluxing overnight. Filter mixture through a pad of CELITE#x0;COMMAT; and rinse with toluene. Concentrate to get 8.7 g yellow oil. Purify the residue by flash chromatography on silica gel eluting with 0-20percent EtOAc/hexanes then 0-30percent ET20/HEXANES to afford the title compound (5.20 g, 58percent). Correct regioisomer is confirmed by NOESY. MS (IS) 450 (M+1) +.
69% With N-iodo-succinimide; trifluoroacetic acid In acetonitrile at 20℃; for 0.833333 h; Inert atmosphere To a solution of 3-methoxyphenol (10, 517.7 mg, 96 percent, 4.0 mmol) in MeCN (16 mL) were added trifluoroacetic acid (0.09 mL, 1.2 mmol) and N-iodosuccinimide (1.424 g, 8.0 mmol). The solution was stirred at ambient temperature for 50 min and quenched with saturated aqueous Na2S2O3 solution. The mixture was extracted three times with EtOAc, and the combined organic layers were dried over MgSO4. The solvents were removed in vacuo, and the residue was purified by flash chromatography (isohexane/DCM/EtOAc 10:2:1) to afford phenol 7 (687.6 mg, 69 percent) as an off-white solid.
52.87% With iodine; silver trifluoroacetate In chloroform at 20℃; for 24 h; (1) 250 mL of a round bottomed flask,I2 (5.1 g, 20.0 mmol) was dissolved in chloroform (150 mL)And stirred for more than 1.5 hours. another,Compound No. 1 (R1 = H) (20.0 mmol) was placed in 250 mL of a round bottomed flask,Silver trifluoroacetate AgOTFA (4.5 g, 20.0 mmol) was added.The chloroform solution was slowly added (about 2-3 hours) into a tin foil-wrapped flask,The reaction was stirred at room temperature for 24 hours. filter,And the residue was washed with chloroform. Then with saturated Na2S2O3 solution,Saturated NaHCO3 solution,Saturated brine, and the resulting organic phase was dried over anhydrous Na2SO4.Filtered and concentrated under reduced pressure and subjected to column chromatography (using CH2Cl2 as eluent and column chromatography).To obtain the product,2-iodo-5-methoxyphenol (Formula 2, R1 = H).The white solid was 52.87percent yield.
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 1, p. 81 - 83
[2] Chemical Communications, 2016, vol. 52, # 29, p. 5152 - 5155
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 9, p. 1956 - 1960
[4] Chemical Communications, 2018, vol. 54, # 39, p. 4935 - 4938
[5] Patent: WO2005/19184, 2005, A1, . Location in patent: Page/Page column 65-66
[6] Chemistry - A European Journal, 2008, vol. 14, # 6, p. 1947 - 1953
[7] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 22, p. 6175 - 6177
[8] Heterocycles, 1997, vol. 45, # 6, p. 1131 - 1142
[9] Organic Letters, 2008, vol. 10, # 13, p. 2701 - 2704
[10] Patent: CN107163011, 2017, A, . Location in patent: Paragraph 0032; 0033
[11] MedChemComm, 2018, vol. 9, # 2, p. 316 - 327
[12] Synthetic Communications, 2013, vol. 43, # 12, p. 1676 - 1682
[13] Collection of Czechoslovak Chemical Communications, 1972, vol. 37, p. 3073 - 3080
[14] Organic and Biomolecular Chemistry, 2007, vol. 5, # 16, p. 2560 - 2563
[15] Patent: WO2005/63739, 2005, A1, . Location in patent: Page/Page column 50-51
  • 39
  • [ 150-19-6 ]
  • [ 7440-44-0 ]
  • [ 41046-70-2 ]
YieldReaction ConditionsOperation in experiment
55% With NaH In methanol; iodine; methyl cyclohexane; toluene a.
2-Iodo-5-methoxyphenol
To a round bottom flask under nitrogen was added 8.4 g (0.174 mole) of 50percent NaH in oil.
The NaH was washed twice with hexane, cooled to 0° C. in ice, and 20.0 g (0.161 mole) of m-methoxyphenol in 200 ml of toluene was added with stirring.
After the evolution of hydrogen was complete 34.1 g (0.134 mole) of iodine dissolved in 600 ml of toluene was added over 30 minutes.
A 100 ml portion of toluene was used to wash in the remaining iodine.
The reaction was stirred for 11/2 hrs., ether was added and the organic layer washed with 3N HCl, water, sodium thiosulfate, brine and dried with MgSO4.
The solvent was evaporated in vacuo and the residue crystallized from 1:1 toluene:methylcyclohexane to give 24.1 g of green solid.
The green solid was stirred with charcoal in methanol for 1/2 hr., the solution filtered, and evaporated in vacuo, and the resulting residue recrystallized in 1:1 toluene:methylcyclohexane to give 19.8 g (55percent yield) of 2-iodo-5-methoxyphenol, mp 70°-72.5° C.
Reference: [1] Patent: US4652584, 1987, A,
  • 40
  • [ 150-19-6 ]
  • [ 22188-03-0 ]
Reference: [1] Patent: US2011/217311, 2011, A1,
  • 41
  • [ 89232-58-6 ]
  • [ 150-19-6 ]
  • [ 824-46-4 ]
  • [ 40925-69-7 ]
  • [ 40925-70-0 ]
Reference: [1] Journal of the American Chemical Society, 1992, vol. 114, # 25, p. 9795 - 9806
  • 42
  • [ 150-19-6 ]
  • [ 63604-94-4 ]
  • [ 102127-34-4 ]
YieldReaction ConditionsOperation in experiment
28% With N-Bromosuccinimide In acetonitrile at 0℃; for 3 h; A solution of 40.0 gm (322.2 mMol) 3-methoxyphenol in 1 L acetonitrile was cooled to 0° C. under a nitrogen atmosphere. To this cooled solution was added a solution of 57.35 gm (322.2 mMol) N-bromosuccinimide in 500 mL acetonitrile dropwise at a rate to maintain the temperature of the reaction mixture at 0° C. (approximately 2 hours). The reaction mixture was stirred at 0° C. for about 1 hour after the addition was complete and was then concentrated under reduced pressure. The residue was treated with carbon tetrachloride and the solid which formed was removed by filtration. The filtrate was concentrated under reduced pressure to provide a mixture of bromination isomers as a red oil.This oil was subjected to silica gel chromatography, eluting with a gradient system of hexane containing from 0-30percent ethyl acetate. Fractions containing the fastest eluting compound were combined and concentrated under reduced pressure to provide 18.1 gm (28percent) of 2-bromo-5-methoxyphenol as a clear liquid.1H-NMR(CDCl3): δ 7.31 (d, 1H), 6.6 (d, 1H), 6.41 (dd, 1H), 5.5 (s, 1H), 3.77 (s, 3H).Fractions containing the later eluting components were combined and concentrated under reduced pressure. This residue was subjected to silica gel chromatography, eluting with dichloromethane. Fractions containing substantially pure 4-bromo-5-methoxyphenol were combined and concentrated under reduced pressure to provide 24.1 gm (37percent) of a white crystalline solid (m.p.=68-69° C.).1H-NMR(CDCl3): δ 7.34 (d, 1H), 6.45 (d, 1H), 6.33 (dd, 1H), 4.9 (br s, 1H), 3.85 (s, 3H).
28% With N-Bromosuccinimide In acetonitrile at 0℃; for 3 h; A solution of 40.0 gm (322.2 mMol) 3-methoxyphenol in 1L acetonitrile was cooled to 0°C under a nitrogen atmosphere. To this cooled solution was added a solution of 57.35 gm (322.2 mMol) N-bromosuccinimide in 500 mL acetonitrile dropwise at a rate to maintain the temperature of the reaction mixture at 0°C (approximately 2 hours). The reaction mixture was stirred at 0°C for about 1 hour after the addition was complete and was then concentrated under reduced pressure. The residue was treated with carbon tetrachloride and the solid which formed was removed by filtration. The filtrate was concentrated under reduced pressure to provide a mixture of bromination isomers as a red oil. This oil was subjected to silica gel chromatography, eluting with a gradient system of hexane containing from 0-30percent ethyl acetate. Fractions containing the fastest eluting compound were combined and concentrated under reduced pressure to provide 18.1 gm (28percent) of 2-bromo-5-methoxyphenol as a clear liquid.1H-NMR(CDCl3): δ 7.31 (d, 1H), 6.6 (d, 1H), 6.41 (dd, 1H), 5.5 (s, 1H), 3.77 (s, 3H). Fractions containing the later eluting components were combined and concentrated under reduced pressure. This residue was subjected to silica gel chromatography, eluting with dichloromethane. Fractions containing substantially pure 4-bromo-5-methoxyphenol were combined and concentrated under reduced pressure to provide 24.1 gm (37percent) of a white crystalline solid (m.p. = 68-69°C).1H-NMR(CDCl3): δ 7.34 (d, 1H), 6.45 (d, 1H), 6.33 (dd, 1H), 4.9 (br s, 1H), 3.85 (s, 3H).
Reference: [1] Synlett, 1997, vol. 1997, # 11, p. 1241 - 1242
[2] Synlett, 1997, vol. 1997, # 11, p. 1241 - 1242
[3] Patent: US7045545, 2006, B1, . Location in patent: Page/Page column 19
[4] Patent: EP1204659, 2003, B1, . Location in patent: Page/Page column 14
[5] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 622 - 627
  • 43
  • [ 150-19-6 ]
  • [ 102127-34-4 ]
YieldReaction ConditionsOperation in experiment
12% With N-Bromosuccinimide In acetonitrile at 20℃; for 18 h; Step 1 : 4-Bromo-3-methoxyphenolTo a solution of 3-methoxyphenol (12.4 g, 100 mmol) in acetonitrile (400 ml) was added solid N-bromosuccinimide (19.5 g, 110 mmol) in portions over 10 minutes. The mixture was stirred at room temperature for 18 hours. The mixture was concentrated in a rotary evaporator and the residue was treated with ether (70 ml). The insoluble material was filtered off. The filtrate was washed with water (40 ml) and the organic layer dried over magnesium sulfate and filtered. The filtrate was concentrated and the residue purified by flash chromatography on silica gel using 0-10percent ethyl acetate/heptane to give the title compound (2.4 g, 12percent).
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 25, p. 4887 - 4890
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2005, vol. 180, # 5-6, p. 1235 - 1240
[3] Synthetic Communications, 2007, vol. 37, # 8, p. 1381 - 1388
[4] Patent: WO2011/34828, 2011, A1, . Location in patent: Page/Page column 82-83
  • 44
  • [ 150-19-6 ]
  • [ 135999-16-5 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 4, p. 1401 - 1408
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 6, p. 1571 - 1579
[3] Journal of the American Chemical Society, 2012, vol. 134, # 17, p. 7305 - 7308
[4] Patent: EP1204659, 2003, B1,
  • 45
  • [ 150-19-6 ]
  • [ 6192-52-5 ]
  • [ 30778-86-0 ]
  • [ 135999-16-5 ]
Reference: [1] Patent: EP1204654, 2003, B1,
[2] Patent: EP1204654, , A1, [2] Patent: , 2002, ,
  • 46
  • [ 150-19-6 ]
  • [ 119138-29-3 ]
Reference: [1] Tetrahedron Letters, 1988, vol. 29, # 32, p. 4005 - 4008
  • 47
  • [ 150-19-6 ]
  • [ 87-13-8 ]
  • [ 6093-72-7 ]
  • [ 93097-22-4 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1984, vol. 38, # 5 B, p. 359 - 366
  • 48
  • [ 150-19-6 ]
  • [ 863309-86-8 ]
Reference: [1] Synthetic Communications, 1996, vol. 26, # 6, p. 1233 - 1245
Recommend Products
Same Skeleton Products
Historical Records