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Chemistry
Heterocyclic Building Blocks
Benzofurans
(2-Butylbenzofuran-3-yl)(4-hydroxyphenyl)methanone
Chemistry
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[ CAS No. 52490-15-0 ] {[proInfo.proName]}

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Chemical Structure| 52490-15-0
Chemical Structure| 52490-15-0
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CAS No. :52490-15-0 MDL No. :MFCD00040947
Formula : C19H18O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 294.34 Pubchem ID :-
Synonyms :

Safety of [ 52490-15-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P312-P322-P330-P363-P501 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 52490-15-0 ]

* 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 [ 52490-15-0 ]

[ 52490-15-0 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 52490-15-0 ]
  • [ 1951-26-4 ]
YieldReaction ConditionsOperation in experiment
98.8% Stage #1: 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran With iodine; potassium carbonate In methanol; water at 40 - 65℃; Stage #2: With hydrogenchloride; sodium sulfite In methanol; water at 20 - 30℃; for 2h; 3.F F. Synthesis of Compounds of Formula 7 100.0 g (0.3397 mol) of the compound shown in Formula 6 and 215.6 g (0.8493 mol) of iodine elemental, 500 g of methanol,300g of water and 61.0g (0.4416mol) of potassium carbonate are mixed and reacted at 40-65°C for 8-10 hours.Add 30.0g (0.2378mol) of sodium sulfite aqueous solution to quench the reaction, and adjust the hydrochloric acid to the system pH of 1-2, 20-30°C,Incubate for 2 hours, and filter by suction to obtain a compound of the formula 7 and dry it at 70-75°C for 6 hours.Compound 183.2g was obtained as a light yellow solid powder with a yield of 98.8%.(Based on the compound represented by Formula 6), the GC purity was 99.6%.
72% With iodine; sodium hydroxide In methanol at 0 - 20℃; for 3h;
With iodine; iodic acid In acetic acid
0.914 g (47%) With hydrogenchloride; sodium hydroxide; iodine In methanol 2.1 2-n-Butyl-3-(4-hydroxy-3,5-diiodobenzoyl)benzofuran Step 1 2-n-Butyl-3-(4-hydroxy-3,5-diiodobenzoyl)benzofuran At 0° C., to a stirred solution containing commercial 2-n-butyl-3-(4-hydroxybenzoyl)benzofuran (1.05 g, 3.57 mmol) and sodium hydroxide (0.286 g, 7.14 mmol) in MeOH (35.7 mL) was added iodine (2.27 g, 8.93 mmol). After 24 h, the reaction was quenched with 1N HCl (30 mL) and extracted with ether. The combined ethereal extracts were washed with 10% aq. Na2 S2 O3 (3*), with brine (3*), dried (MgSO4) and concentrated. The crude product was purified on Biotage KP-Sil to give 0.914 g (47%) of the title compound. 1 H NMR (DMSO-d6) δ 0.85 (t, 3 H), 1.27 (sextet, 2 H), 1.71 (quintet, 2 H), 2.77 (t, 2 H), 7.29-7.36 (m, 2 H), 7.45 (d, 1 H), 7.65 (d, 1 H), 8.11 (s, 2 H), 10.5 (br s, 1 H).
14.61 g With iodine; potassium carbonate In ethanol for 2h; Reflux; 1.4 4,Synthesis of 2-butyl-(4-hydroxy-3,5-diiodobenzoyl)benzofuran: Add to the 100 ml reaction bottle8 g of 2-butyl-(4-hydroxybenzoyl)benzofuran,15.18 grams of iodine,8.26 g of potassium carbonate and 48 ml of ethanol,The mixture was heated to reflux under stirring, and the reaction was kept for 2 hours, and the reaction was completed.Cool down to room temperature, filter, add the filtrate to the aqueous solution of sodium metabisulfite,After the completion of the dropwise addition, the mixture was stirred for 0.5 hour, filtered, and the filter cake was washed twice with water.The solid was dried under vacuum to give a white solid, 14.61 g.

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN107382925, 2017, A Location in patent: Paragraph 0065-0067; 0095-0097; 0125-0127
[2]Huang, Wenbo; Xu, Jing; Liu, Changhui; Chen, Zhiyan; Gu, Yanlong [Journal of Organic Chemistry, 2019, vol. 84, # 5, p. 2941 - 2950]
[3]Ha; Stieger; Grassi; Altorfer; Follath [European Journal of Clinical Pharmacology, 2000, vol. 55, # 11-12, p. 807 - 814]
[4]Current Patent Assignee: PFIZER INC - US6103708, 2000, A
[5]Current Patent Assignee: ZHEJIANG POLY PHARMACEUTICAL; HAINAN POLY PHARMACEUTICAL - CN109988131, 2019, A Location in patent: Paragraph 0016
  • 2
  • [ 83790-87-8 ]
  • [ 52490-15-0 ]
YieldReaction ConditionsOperation in experiment
100% aluminium chloride; In 1,1-dichloroethane; water; a) 2-n-butyl 3-(4-hydroxy benzoyl) benzofuran To a solution of 2 g (6.5 mmoles) of 2-n-butyl 3-(4-methoxy benzoyl) benzofuran in 30 ml of dichloroethane 1.82 g (13.6 mmoles) of aluminium chloride are added under argon. The mixture is heated at reflux for 9 hours, then cooled to room temperature. The reaction mixture is then poured into 50 ml of water, stirred vigorously for 30 minutes, then the organic phase is separated. It is washed 3 times with 30 ml of water, dried over sodium sulfate and decolorized by means of diatomaceous earth. After evaporation of the solvent, 1.9 g (6.5 mmoles) of 2-n-butyl 3-(4-hydroxy benzoyl) benzofuran are obtained. Yield: 100% M.p.: 119-120 C.
91.6% With aluminum (III) chloride; In chlorobenzene; at 80℃; for 2h;Inert atmosphere; To a solution of compound 3 (1.9 g,5.46 mmol) in chlorobenzene (11 mL) was added AlCl3 (2.2 g, 16.38 mmol).The mixture was stirred at 80 C for 2 hours and was quenched with ice water(20 mL). The reaction mixture was extracted withEA (330 mL). The organicphase was dried over Na2SO4, filtered and concentrated togive the crude product, which was purified by flash chromatography [PE/EA=5:1]to give 4 (1.46g, 78.5%) asa yellow solid. 1H NMR (400 MHz, CDCl3)δ 8.32 (dd, J = 2.4, 0.5 Hz, 1H), 8.22 - 8.18 (m, 1H), 7.79 - 7.75 (m, 2H),7.55 (dd, J = 9.0, 0.5 Hz, 1H), 6.97 - 6.93 (m, 2H), 2.90 (dd, J = 8.1, 7.1 Hz,2H), 1.78 - 1.70 (m, 2H), 1.37 - 1.29 (m, 2H), 0.86 (t, J = 7.3 Hz, 3H).
Ca. 86.9% With aluminum (III) chloride; In toluene; at 80 - 90℃;Large scale; 20.00 kg (64.9 mol, 1.0 eq) of compound 8 was added to 60.00 kg (3 w/w) of toluene.9.52 kg (71.4 mol, 1.1 eq) of aluminum trichloride was added and the reaction was carried out at 80 to 90 C for 2 to 4 hours.After the reaction, the reaction solution was transferred to 90.00 kg (4.5 w/w) of purified water.Adjust the pH to 2 with dilute hydrochloric acid, and wash the organic phase with 50.00 kg (2.5 w/w) of purified water twice.The organic phase was washed with 50.00 kg (2.5 w/w) saturated aqueous sodium chloride solution.It was dried by adding 2.00 kg (0.1 w/w) anhydrous sodium sulfate.The organic phase was concentrated under reduced pressure at 65 C until a solid precipitated, cooled to 0 C, and then allowed to crystallize for 4 hours.Vacuum filtration, wet drying at 80 C,A white crystalline powder of 16.60 kg (56.4 mol) of Compound 9 was obtained in a yield of about 86.9%.
55% With sodium thioethylate; In N,N-dimethyl-formamide; at 110℃; for 16h; In a RBF (100 mL) containing a SB, 86 (400 mg5 1.30 mmol) was diluted with DMF (18.0 mL) and NaSEt (0.426 g, 5.19 mmol) was added. The reaction mixture was heated to 110 C and stirred (16 h). The reaction was quenched by the addition of sat. NH4C1, and was extracted with EtOAc (4 x 25 mL). The combined organic layers were washed with brine, dried (Na2S04), filtered and concentrated in vacuo. The crude material was purified by column chromatography on Si02 (Hex: EtOAc; 4:1) to afford 87 (0.210 mg, 0.713 mmol, 55%) as a light yellow oil. 1H- NMR (400 MHz) CDC13: 7.81-7.78 (d, 2 H), 7.48-7.46 (d, 1 H), 7.37-7.36 (d, 1 H), 7.29-7.25 (m, 1 H), 7.20-7.16 (m, 1 H), 6.94-6.90 (d, 2 H), 6.56 (bs, 1 H), 2.93-2.89 (t, 2 H) 1.79-1.71 (m, 2 H), 1.38-1.32 (m, 2 H), 0.90-0.86 (t, 3 H); 13C-NMR (100 MHz) CDC13: 191.2, 165.0, 160.4, 153.6, 132.1, 131.6, 127.1 , 124.2, 123.4, 121.2, 1 16.7, 1 15.4, 1 1 1.0, 30.1, 27.9, 22.3, 13.7. LC/MS-MS: 295.0 121.2 m/z; GS1 and GS2 at 30, DP = 56, CE = 31 , CXP = 6, tR = 4.51 min.
82.3 g With boron trifluoride diethyl etherate; In acetonitrile; at 80℃; for 2h; 110.9 g (0.36 mol) of 2-butyl-3- (4-methoxybenzoyl) benzofuran obtained in step (1) was charged into a reactor equipped with a magnetic stirrer,Boron trifluoride ether 10.2 g (72 mmol)Soluble in 2L acetonitrile;The mixture was stirred at 80 C for 2 hours,The organic phase is combined and then concentrated under reduced pressure; the recrystallization of ethyl acetate and ether is carried out to obtain the same as that of the ethyl acetate and the ethyl acetate solution,2-butyl-3- (4-hydroxybenzoyl) benzofuran82.3 g (0.28 mol).
8.16 g With aluminum (III) chloride; In toluene; for 6h;Reflux; Add to the 100 ml reaction bottle10.00 g of 2-butyl-(4-methoxybenzoyl)benzofuran,4.50 g of aluminum trichloride and 40 ml of toluene,The temperature was raised to reflux, and the reaction was kept for 6 hours, and the reaction was completed.Cool down to 0 C, pour into ice water, separate the liquid, extract the aqueous phase with toluene, and combine the organic phases.Add an equal volume of water, adjust the pH to above 12 with NaOH solution, and dispense.The aqueous phase is adjusted to pH less than 3 with hydrochloric acid and filtered.The filter cake was dried in vacuo to give a pale yellow solid, 8.16 g.

Reference： [1]Patent: US5266711,1993,A
[2]Bioorganic and Medicinal Chemistry Letters,2021,vol. 46
[3]Patent: CN109053652,2018,A .Location in patent: Paragraph 0019; 0055; 0061; 0064; 0070; 0079; 0081
[4]Journal of Organic Chemistry,2019,vol. 84,p. 2941 - 2950
[5]Patent: WO2012/48058,2012,A2 .Location in patent: Page/Page column 43
[6]Patent: CN106946822,2017,A .Location in patent: Paragraph 0028; 0034; 0040; 0046-0047; 0052
[7]Patent: CN109988131,2019,A .Location in patent: Paragraph 0015
  • 3
  • [ 7757-82-6 ]
  • [ 52490-15-0 ]
  • [ 106-93-4 ]
  • 2-n-butyl-3-[4-(2-bromo-ethoxy)-benzoyl]-benzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With sodium hydroxide; potassium carbonate; In diethyl ether; butanone; (a) 2-n-Butyl-3-[4-(2-bromo-ethoxy)-benzoyl]-benzofuran A mixture of 93.5 g (0.25 mole) of 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran, 69 g (0.5 mole) of finely ground anhydrous potassium carbonate and 500 ml of methyl ethyl ketone was stirred and refluxed for 30 minutes. The mixture was allowed to cool to about 50 C. and 187.8 g (1 mole) of 1,2-dibromo-ethane were added in one operation. Stirring and refluxing were continued for 18 h and a further increment of 47 g of 1,2-dibromo-ethane was added. Refluxing was continued for 6 h, the course of the reaction being monitored by thin-layer chromatography (TLC). Filtration and evaporation to dryness under reduced pressure then followed. The residue was taken up in diethyl ether after which the ethereal solution was washed, first with water, then with a 10% aqueous solution of sodium hydroxide and once again with water. Drying was carried out over <strong>[7757-82-6]sodium sulphate</strong>, followed by evaporation to dryness under reduced pressure. In this way 56.5 g of 2-n-butyl-3-[ 4-(2-bromo-ethoxy)-benzoyl]-benzofuran in the form of an oil were obtained. Yield: 60% M.P.: 46-47 C. (isopropanol)
Reference： [1]Patent: US4565828,1986,A
  • 4
  • [ 52490-15-0 ]
  • 2-n-butyl-3-(3-iodo-4-hydroxybenzoyl)-benzofuran [ No CAS ]
  • [ 1951-26-4 ]
YieldReaction ConditionsOperation in experiment
1: 25% 2: 11% With potassium hydroxide; sodium hypochlorite; sodium iodide In methanol at -5℃; for 4h;
Reference： [1]Snead, Aaron N.; Miyakawa, Motonori; Tan, Edwin S.; Scanlan, Thomas S. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 22, p. 5920 - 5922]
  • 5
  • [ 52490-15-0 ]
  • [ 93-00-5 ]
  • C29H24N2O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: Bronner acid With hydrogenchloride; sodium nitrite at 0 - 5℃; for 0.5h; Stage #2: 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran With sodium hydroxide at 0 - 20℃; for 2.5h;
Reference： [1]Patel, Hitendra M. [Journal of the Serbian Chemical Society, 2012, vol. 77, # 11, p. 1551 - 1560]
  • 6
  • [ 52490-15-0 ]
  • [ 81-16-3 ]
  • C29H24N2O6S [ No CAS ]
Reference： [1]Journal of the Serbian Chemical Society,2012,vol. 77,p. 1551 - 1560

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