Name: 56317-21-6|5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol|98%
Brand: Ambeed
SKU: A904366
Rating: 91 (27 reviews)

1
[ 112768-54-4 ]
[ 112768-53-3 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Yield given. Multistep reaction;

Reference： [1]Matsuyama, Shigeru; Kuwahara, Yasumasa; Nakamura, Shigeko; Suzuki, Takahisa [Agricultural and Biological Chemistry, 1991, vol. 55, # 5, p. 1333 - 1341]

2
[ 112768-55-5 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	With tetrabutyl ammonium fluoride In tetrahydrofuran for 48h; Ambient temperature;
86%	With tetrabutyl ammonium fluoride In tetrahydrofuran for 16h; Ambient temperature;

Reference： [1]Clough, John M.; Mann, Inderjit S.; Widdowson, David A. [Tetrahedron Letters, 1987, vol. 28, # 23, p. 2645 - 2648]
[2]Mann, Inderjit S.; Widdowson, David A.; Clough, John M. [Tetrahedron, 1991, vol. 47, # 37, p. 7981 - 7990]

3
[ 134937-20-5 ]
[ 56317-21-6 ]
[ 134979-08-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 22% 2: 18%	With boron tribromide In dichloromethane for 480h; Ambient temperature;

Reference： [1]Watanabe; Kawanishi; Furukawa [Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 3, p. 579 - 583]

4
[ 134937-19-2 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
12.3%	With formic acid for 1h; Heating;

Reference： [1]Watanabe; Kawanishi; Furukawa [Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 3, p. 579 - 583]

5
[ 56317-21-6 ]
[ 74-88-4 ]
[ 73343-39-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate In acetone Heating;

Reference： [1]Watanabe; Kawanishi; Furukawa [Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 3, p. 579 - 583]

Yield	Reaction Conditions	Operation in experiment
	Oxyresveratrol-tetraacetat, 1) Br2, 2) KOH in CH3OH, 3) HOAc;

7
[ 863310-53-6 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In ethanol

Reference： [1]Kinoshita, Takeshi; Ichinose, Koji [Heterocycles, 2005, vol. 65, # 7, p. 1641 - 1654]

8
3-(3,5-bis-benzyloxy-phenyl)-7-hydroxy-chromen-2-one [ No CAS ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: K₂CO₃ / acetone 2: LAH; AlCl₃ / diethyl ether; tetrahydrofuran / 1.5 h 3: 11 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 7.5 h / Heating 4: hydrogen / Pd-C / ethanol

Reference： [1]Kinoshita, Takeshi; Ichinose, Koji [Heterocycles, 2005, vol. 65, # 7, p. 1641 - 1654]

9
[ 863310-42-3 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: LAH; AlCl₃ / diethyl ether; tetrahydrofuran / 1.5 h 2: 11 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 7.5 h / Heating 3: hydrogen / Pd-C / ethanol

Reference： [1]Kinoshita, Takeshi; Ichinose, Koji [Heterocycles, 2005, vol. 65, # 7, p. 1641 - 1654]

10
[ 863310-61-6 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 11 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 7.5 h / Heating 2: hydrogen / Pd-C / ethanol

Reference： [1]Kinoshita, Takeshi; Ichinose, Koji [Heterocycles, 2005, vol. 65, # 7, p. 1641 - 1654]

11
[ 2732-96-9 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: KOAc / acetic anhydride / 10 h / 150 °C 2: K₂CO₃ / acetone 3: LAH; AlCl₃ / diethyl ether; tetrahydrofuran / 1.5 h 4: 11 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 7.5 h / Heating 5: hydrogen / Pd-C / ethanol

Reference： [1]Kinoshita, Takeshi; Ichinose, Koji [Heterocycles, 2005, vol. 65, # 7, p. 1641 - 1654]

12
[ 95-01-2 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: KOAc / acetic anhydride / 10 h / 150 °C 2: K₂CO₃ / acetone 3: LAH; AlCl₃ / diethyl ether; tetrahydrofuran / 1.5 h 4: 11 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 7.5 h / Heating 5: hydrogen / Pd-C / ethanol
	Multi-step reaction with 4 steps 1.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 2.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 2.2: 0.08 h / 0 °C 2.3: 14.5 h / 0 - 20 °C 3.1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 4.1: boron tribromide / dichloromethane
	Multi-step reaction with 4 steps 1: dmap; triethylamine / dichloromethane 2: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 3: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 4: boron tribromide / dichloromethane

	Multi-step reaction with 5 steps 1.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 2.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 2.2: 0.08 h / 0 °C 2.3: 14.5 h / 0 - 20 °C 3.1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 4.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 5.1: boron tribromide / dichloromethane / 24 h / -78 - 20 °C
	Multi-step reaction with 5 steps 1: dmap; triethylamine / dichloromethane 2: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 3: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 4: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 5: boron tribromide / dichloromethane / 24 h / -78 - 20 °C
	Multi-step reaction with 3 steps 1.1: triphenylphosphine; zinc / acetonitrile / 1 h / 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: caesium carbonate; copper(l) iodide / acetonitrile / 3 h / 80 °C / Inert atmosphere 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate / water; N,N-dimethyl-formamide / 1 h / Inert atmosphere; Heating

Reference： [1]Kinoshita, Takeshi; Ichinose, Koji [Heterocycles, 2005, vol. 65, # 7, p. 1641 - 1654]
[2]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[3]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[4]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[5]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[6]Sivaraman, Aneesh; Harmalkar, Dipesh S.; Kang, Jiyoon; Choi, Yongseok; Lee, Kyeong [Organic and Biomolecular Chemistry, 2019, vol. 17, # 8, p. 2153 - 2161]

13
[ 13196-11-7 ]
[ 56317-21-6 ]

Reference： [1]Tetrahedron,1991,vol. 47,p. 7981 - 7990
[2]Agricultural and Biological Chemistry,1991,vol. 55,p. 1333 - 1341
[3]Tetrahedron Letters,1987,vol. 28,p. 2645 - 2648

14
[ 50551-63-8 ]
[ 56317-21-6 ]

Reference： [1]Tetrahedron,1991,vol. 47,p. 7981 - 7990

15
[ 112768-54-4 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1) BuLi, Me₃SnCl, 2) Pd(PPh₃)4 / 1) THF, rt, 1 h, 2) THF, reflux 2: 86 percent / Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

Reference： [1]Mann, Inderjit S.; Widdowson, David A.; Clough, John M. [Tetrahedron, 1991, vol. 47, # 37, p. 7981 - 7990]

16
[ 108-46-3 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / acetonitrile 2.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 3.2: 0.08 h / 0 °C 3.3: 14.5 h / 0 - 20 °C 4.1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 5.1: boron tribromide / dichloromethane
	Multi-step reaction with 5 steps 1: trichlorophosphate / acetonitrile 2: dmap; triethylamine / dichloromethane 3: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 4: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 5: boron tribromide / dichloromethane
	Multi-step reaction with 6 steps 1.1: trichlorophosphate / acetonitrile 2.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 3.2: 0.08 h / 0 °C 3.3: 14.5 h / 0 - 20 °C 4.1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 6.1: boron tribromide / dichloromethane / 24 h / -78 - 20 °C

Multi-step reaction with 6 steps 1: trichlorophosphate / acetonitrile 2: dmap; triethylamine / dichloromethane 3: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 4: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 5: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 6: boron tribromide / dichloromethane / 24 h / -78 - 20 °C

Reference： [1]Matsuyama, Shigeru; Kuwahara, Yasumasa; Nakamura, Shigeko; Suzuki, Takahisa [Agricultural and Biological Chemistry, 1991, vol. 55, # 5, p. 1333 - 1341]
[2]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[3]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[4]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[5]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]

17
[ 2150-44-9 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 82 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 3: 12.3 percent / 90percent HCO₂H / 1 h / Heating

Reference： [1]Watanabe; Kawanishi; Furukawa [Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 3, p. 579 - 583]

18
[ 2150-37-0 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 2: 52 percent / 90percent HCO₂H / 1 h / Heating 3: 18 percent / BBr₃ / CH₂Cl₂ / 480 h / Ambient temperature

Reference： [1]Watanabe; Kawanishi; Furukawa [Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 3, p. 579 - 583]

19
[ 132552-87-5 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 2: 52 percent / 90percent HCO₂H / 1 h / Heating 3: 18 percent / BBr₃ / CH₂Cl₂ / 480 h / Ambient temperature
	Multi-step reaction with 2 steps 1: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 2: 12.3 percent / 90percent HCO₂H / 1 h / Heating

Reference： [1]Watanabe; Kawanishi; Furukawa [Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 3, p. 579 - 583]
[2]Watanabe; Kawanishi; Furukawa [Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 3, p. 579 - 583]

20
[ 103929-83-5 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 2: 12.3 percent / 90percent HCO₂H / 1 h / Heating

Reference： [1]Watanabe; Kawanishi; Furukawa [Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 3, p. 579 - 583]

21
[ 134937-22-7 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 52 percent / 90percent HCO₂H / 1 h / Heating 2: 18 percent / BBr₃ / CH₂Cl₂ / 480 h / Ambient temperature

Reference： [1]Watanabe; Kawanishi; Furukawa [Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 3, p. 579 - 583]

22
[ 112768-53-3 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: 86 percent / TBAF / tetrahydrofuran / 48 h / Ambient temperature

Reference： [1]Clough, John M.; Mann, Inderjit S.; Widdowson, David A. [Tetrahedron Letters, 1987, vol. 28, # 23, p. 2645 - 2648]

23
[ 1332302-64-3 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
2.1 mg	In [D₃]acetonitrile at 80℃; for 8h;

Reference： [1]Celaje, Jeff A.; Zhang, Dong; Guerrero, Angela M.; Selke, Matthias [Organic Letters, 2011, vol. 13, # 18, p. 4846 - 4849]

24
[ 50841-50-4 ]
[ 108-46-3 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aluminum oxide / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / Reflux 2: boron tribromide / dichloromethane / 0 - 20 °C / Inert atmosphere

Reference： [1]Arias, Leire; Vara, Yosu; Cossio, Fernando P. [Journal of Organic Chemistry, 2012, vol. 77, # 1, p. 266 - 275]

25
[ 73343-39-2 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: 2-(3,5-dimethoxyphenyl)-6-methoxybenzofuran With boron tribromide In dichloromethane at -78 - 25℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With water In dichloromethane Schlenk technique; Inert atmosphere; Cooling with ice;
70%	With boron tribromide In dichloromethane at -78 - 20℃; for 3h; Inert atmosphere;	7-(6-Hydroxybenzofuran-2-yl)-2,2-dimethylchroman-5-ol,Wittifuran D (11): General procedure: To a stirred solutionof 8 (100 mg, 0.28 mmol) in dry DCM (4 mL) at 78 C under nitrogen conditions wasadded dropwise 1-M BBr3 solution in CH2Cl2 (1.4 mL, 1.42 mmol) and stirred at the sametemperature for 2 h, then room temperature for 1 h. After completion of the reaction, theexcess BBr3 was quenched by adding ice water at 0 C. The reaction mixture was warmedto room temperature and extracted with ethyl acetate 2 times. The combined organic layerwas dried over MgSO4, filtered, and evaporated. The residue was purified by silica gelcolumn chromatography (Hex:EtOAc = 7:3, v/v) to afford compound 11 (50 mg, 60% yield)as a white solid:
	Stage #1: 2-(3,5-dimethoxyphenyl)-6-methoxybenzofuran With boron tribromide In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; Stage #2: With methanol In dichloromethane at 0℃;	13 Example 13: Preparation of 5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol, with the following structural formula: [Show Image]; This compound was prepared using Method A from resorcinol and 2-bromo-1-(3,5-dimethoxyphenyl)ethanone: Yield 25% following procedures A.2 and A.5; m.p. 168°C (dec.); IR 3355, 2931, 1613, 1432, 1293, 1145 cm-1; 1H-NMR (500 MHz, δ ppm, DMSO-d6) 9.52 (s, 1H), 9.37 (s, 2H), 7.38 (d, J = 8.4 Hz, 1H), 7.06 (s, 1H), 6.92 (s, 1H), 6.74 (d, J = 8.3 Hz, 1H), 6.68 (s, 2H), 6.21 (s, 1H); 13C-NMR (126 MHz, δ ppm, CD3O) 160.1, 157.4, 156.9, 156.3, 133.9, 123.2, 122.1, 113.4, 104.1, 103.7, 102.3, 98.6.

Reference： [1]Che, Chi-Ming; Wu, Kai; Wu, Liang-Liang; Zhou, Cong-Ying [Angewandte Chemie - International Edition, 2020, vol. 59, # 37, p. 16202 - 16208][Angew. Chem., 2020, vol. 132, # 37, p. 16336 - 16342,7]
[2]BasavanaGowda, Melanayakanakatte Kuberappa; Chae, Hee-Sung; Choi, Won Jun; Masagalli, Jagadeesh Nagarajappa [Molecules, 2021, vol. 26, # 5]
[3]Current Patent Assignee: UNIVERSITY OF THE BASQUE COUNTRY; IKERCHEM - EP2388255, 2011, A1 Location in patent: Page/Page column 20-21

26
[ 134937-20-5 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With aluminum (III) chloride In chloroform at 65℃; for 9h;	1.4 Example 1 2- (3,5-Dimethoxyphenyl) -6-hydroxybenzofuran (10 mmol, 2.70 g), aluminum trichloride(40 mmol, 5.33 g) was added to 50 ml of chloroform, stirred, heated to 65 ° C, 9 h reaction;After completion, the solution was cooled to room temperature, filtered, washed with water (10 ml x 3), dried over anhydrous magnesium sulfate and concentrated.The alcohol was recrystallized to give 2.23 g of white Moracin M as a solid in 92% yield.
88%	With boron tribromide In dichloromethane at -78 - 20℃; for 8h; Inert atmosphere; Schlenk technique;
88%	With boron tribromide In dichloromethane at -78 - 20℃; for 8h; Inert atmosphere;	27.2 (2) Take 2- (3,5-dimethoxyphenyl) benzofuran-6-phenol (M18, 40.5mg, 0.15mmol, 1.0eq.)5 ml of dry methylene chloride was added, and boron tribromide (3.0 eq., 1 mmol / mL methylene chloride solution) was added dropwise under a nitrogen atmosphere at -78 ° C, and the reaction was raised to room temperature and stirred for 8 hours. Slowly add 2 mL of water to quench the reaction. Extracted with ethyl acetate (10mL x 3), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (eluent PE / EA = 10/1) to obtain the product Moracin M (P4-3) (32mg, 88%). Characteristic data is consistent with literature data.

86%	With aluminum (III) chloride In 1,2-dichloro-ethane at 80℃;
26%	With aluminum oxide In 5,5-dimethyl-1,3-cyclohexadiene for 16h; Reflux;
25%	With boron tribromide In dichloromethane at 0 - 20℃; Inert atmosphere;
25%	With boron tribromide In dichloromethane at 0℃;
25%	With boron tribromide In dichloromethane
	Multi-step reaction with 2 steps 1: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C 2: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 36 h / Inert atmosphere; Reflux
	Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 2: boron tribromide / dichloromethane / 24 h / -78 - 20 °C

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN104447646, 2016, B Location in patent: Paragraph 0034
[2]Cao, Tongxiang; Jiang, Huanfeng; Zhang, Ling; Zhu, Shifa [Angewandte Chemie - International Edition, 2020, vol. 59, # 12, p. 4670 - 4677][Angew. Chem., 2020, vol. 132, p. 4700 - 4707,8]
[3]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY; GENIFARM GUANGZHOU TECH; XINYUAN GUANGZHOU PHARMACEUTICAL RES - CN110894192, 2020, A Location in patent: Paragraph 0164-0166; 0168
[4]Xu, Tianlong; Zhang, Ensheng; Wang, Dejian; Wang, Yan; Zou, Yong [Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4313 - 4324]
[5]Lee, Ju Hee; Ko, Hae Ju; Woo, Eun-Rhan; Lee, Sang Kook; Moon, Bong Soo; Lee, Chan Woo; Mandava, Suresh; Samala, Mallesham; Lee, Jongkook; Kim, Hyun Pyo [European Journal of Pharmacology, 2016, vol. 783, p. 64 - 72]
[6]Location in patent: experimental part Arias, Leire; Vara, Yosu; Cossio, Fernando P. [Journal of Organic Chemistry, 2012, vol. 77, # 1, p. 266 - 275]
[7]Lee, Jae Jun; Yun, So-Ra; Jun, Jong-Gab [Bulletin of the Korean Chemical Society, 2014, vol. 35, # 12, p. 3453 - 3458]
[8]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[9]Wu, Deyan; Mei, Hanbing; Tan, Ping; Lu, Weiqiang; Zhu, Jin; Wang, Wei; Huang, Jin; Li, Jian [Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387]
[10]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]

27
[ 6626-15-9 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triethylamine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: palladium diacetate; copper(l) iodide; tri tert-butylphosphoniumtetrafluoroborate / 72 h / 40 °C / Inert atmosphere 3.1: potassium hydroxide; water / methanol / 5 h / Inert atmosphere; Reflux 4.1: boron tribromide / dichloromethane / 0 °C

Reference： [1]Lee, Jae Jun; Yun, So-Ra; Jun, Jong-Gab [Bulletin of the Korean Chemical Society, 2014, vol. 35, # 12, p. 3453 - 3458]

28
[ 66417-41-2 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: palladium diacetate; copper(l) iodide; tri tert-butylphosphoniumtetrafluoroborate / 72 h / 40 °C / Inert atmosphere 2: potassium hydroxide; water / methanol / 5 h / Inert atmosphere; Reflux 3: boron tribromide / dichloromethane / 0 °C

Reference： [1]Lee, Jae Jun; Yun, So-Ra; Jun, Jong-Gab [Bulletin of the Korean Chemical Society, 2014, vol. 35, # 12, p. 3453 - 3458]

29
1-(2,4-diacetoxyphenyl)-2-(3,5-dimethoxyphenyl)acetylene [ No CAS ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hydroxide; water / methanol / 5 h / Inert atmosphere; Reflux 2: boron tribromide / dichloromethane / 0 °C

Reference： [1]Lee, Jae Jun; Yun, So-Ra; Jun, Jong-Gab [Bulletin of the Korean Chemical Society, 2014, vol. 35, # 12, p. 3453 - 3458]

30
(E)-2-(2-bromo-4-hydroxyphenyl)-3-(3,5-dimethoxyphenyl)acrylic acid [ No CAS ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper diacetate; potassium hydroxide; 1,10-Phenanthroline; oxygen / water; dimethyl sulfoxide / 1 h / 110 °C / Microwave irradiation 2: 1,10-Phenanthroline; copper(l) iodide / 0.17 h / 180 °C / Microwave irradiation 3: aluminum (III) chloride / 1,2-dichloro-ethane / 80 °C

Reference： [1]Xu, Tianlong; Zhang, Ensheng; Wang, Dejian; Wang, Yan; Zou, Yong [Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4313 - 4324]

31
2-(3,5-dimethoxyphenyl)-6-hydroxybenzofuran-3-carboxylic acid [ No CAS ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1,10-Phenanthroline; copper(l) iodide / 0.17 h / 180 °C / Microwave irradiation 2: aluminum (III) chloride / 1,2-dichloro-ethane / 80 °C

Reference： [1]Xu, Tianlong; Zhang, Ensheng; Wang, Dejian; Wang, Yan; Zou, Yong [Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4313 - 4324]

32
[ 88491-44-5 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C 2: copper diacetate; potassium hydroxide; 1,10-Phenanthroline; oxygen / water; dimethyl sulfoxide / 1 h / 110 °C / Microwave irradiation 3: 1,10-Phenanthroline; copper(l) iodide / 0.17 h / 180 °C / Microwave irradiation 4: aluminum (III) chloride / 1,2-dichloro-ethane / 80 °C
	Multi-step reaction with 4 steps 1: acetic anhydride; triethylamine / 7 h / 110 °C 2: copper diacetate; 1,10-Phenanthroline; potassium hydroxide / dimethyl sulfoxide; water / 1 h / 120 °C / Microwave irradiation 3: copper(II) oxide; 8-quinolinol; 1,10-Phenanthroline / 0.13 h / 200 °C / Microwave irradiation 4: aluminum (III) chloride / chloroform / 9 h / 65 °C

Reference： [1]Xu, Tianlong; Zhang, Ensheng; Wang, Dejian; Wang, Yan; Zou, Yong [Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4313 - 4324]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN104447646, 2016, B

33
[ 7311-34-4 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C 2: copper diacetate; potassium hydroxide; 1,10-Phenanthroline; oxygen / water; dimethyl sulfoxide / 1 h / 110 °C / Microwave irradiation 3: 1,10-Phenanthroline; copper(l) iodide / 0.17 h / 180 °C / Microwave irradiation 4: aluminum (III) chloride / 1,2-dichloro-ethane / 80 °C
	Multi-step reaction with 4 steps 1: acetic anhydride; triethylamine / 7 h / 110 °C 2: copper diacetate; 1,10-Phenanthroline; potassium hydroxide / dimethyl sulfoxide; water / 1 h / 120 °C / Microwave irradiation 3: copper(II) oxide; 8-quinolinol; 1,10-Phenanthroline / 0.13 h / 200 °C / Microwave irradiation 4: aluminum (III) chloride / chloroform / 9 h / 65 °C

Reference： [1]Xu, Tianlong; Zhang, Ensheng; Wang, Dejian; Wang, Yan; Zou, Yong [Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4313 - 4324]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN104447646, 2016, B

34
[ 299912-77-9 ]
[ 56317-21-6 ]

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4383 - 4387

35
(1-benzofuran-6-yloxy)(tert-butyl)dimethylsilane [ No CAS ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: -78 - 20 °C 1.3: 20 °C / pH 5 2.1: potassium carbonate; palladium diacetate; tricyclohexylphosphine / water; 1,2-dimethoxyethane / 2 h / 80 °C / Inert atmosphere 3.1: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C 4.1: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 36 h / Inert atmosphere; Reflux

Reference： [1]Wu, Deyan; Mei, Hanbing; Tan, Ping; Lu, Weiqiang; Zhu, Jin; Wang, Wei; Huang, Jin; Li, Jian [Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387]

36
(6-[tert-butyl(dimethyl)silyl]oxy}-1-benzofuran-2-yl)boronic acid [ No CAS ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate; palladium diacetate; tricyclohexylphosphine / water; 1,2-dimethoxyethane / 2 h / 80 °C / Inert atmosphere 2: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C 3: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 36 h / Inert atmosphere; Reflux

Reference： [1]Wu, Deyan; Mei, Hanbing; Tan, Ping; Lu, Weiqiang; Zhu, Jin; Wang, Wei; Huang, Jin; Li, Jian [Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387]

37
[ 218444-38-3 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With n-butyllithium; diphenylphosphane In tetrahydrofuran; hexane for 36h; Inert atmosphere; Reflux;	5-(6-Hydroxybenzofuran-2-yl)-2-(3-methyl-2-butenyl)-1,3-benzenediol (1) General procedure: ). n-Butyllithium (2.4 M inhexane, 2.25 mL, 5.4 mmol) was added over 1 h to a stirred solution ofdiphenylphosphine (940 μL, 5.4 mmol) in dry THF (8 mL) at 0°C under nitrogen. 34 (404 mg, 0.9 mmol) in dry THF (4 mL) wasadded and the solution was allowed to warm to room temperature. The mixture washeated under reflux for 36 h and was then poured into 4 M aqueous sodiumhydroxide (8 mL), acidified with 4 M aqueous HCl and extracted into ethylacetate. The organic extract was dried with anhydrous sodium sulfate and thesolvent removed in vacuo.

Reference： [1]Wu, Deyan; Mei, Hanbing; Tan, Ping; Lu, Weiqiang; Zhu, Jin; Wang, Wei; Huang, Jin; Li, Jian [Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387]

38
[ 6272-26-0 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 1H-imidazole / tetrahydrofuran / 4 h / 0 - 20 °C 2.1: sodium tetrahydroborate / methanol / 4 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: -78 - 20 °C 3.3: 20 °C / pH 5 4.1: potassium carbonate; palladium diacetate; tricyclohexylphosphine / water; 1,2-dimethoxyethane / 2 h / 80 °C / Inert atmosphere 5.1: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C 6.1: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 36 h / Inert atmosphere; Reflux

Reference： [1]Wu, Deyan; Mei, Hanbing; Tan, Ping; Lu, Weiqiang; Zhu, Jin; Wang, Wei; Huang, Jin; Li, Jian [Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387]

39
2-(2-bromo-4-hydroxyphenyl)-3-(3,5-dimethoxyphenyl)acrylic acid [ No CAS ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper diacetate; 1,10-Phenanthroline; potassium hydroxide / dimethyl sulfoxide; water / 1 h / 120 °C / Microwave irradiation 2: copper(II) oxide; 8-quinolinol; 1,10-Phenanthroline / 0.13 h / 200 °C / Microwave irradiation 3: aluminum (III) chloride / chloroform / 9 h / 65 °C

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN104447646, 2016, B

40
tris(3,5-dimethoxyphenyl)bismuthine [ No CAS ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: boron tribromide / dichloromethane
	Multi-step reaction with 2 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: boron tribromide / dichloromethane
	Multi-step reaction with 3 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: boron tribromide / dichloromethane / 24 h / -78 - 20 °C

Multi-step reaction with 3 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: boron tribromide / dichloromethane / 24 h / -78 - 20 °C

Reference： [1]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[2]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[3]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[4]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]

41
[ 52924-53-5 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 1.2: 0.08 h / 0 °C 1.3: 14.5 h / 0 - 20 °C 2.1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 3.1: boron tribromide / dichloromethane
	Multi-step reaction with 4 steps 1.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 1.2: 0.08 h / 0 °C 1.3: 14.5 h / 0 - 20 °C 2.1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 3.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 4.1: boron tribromide / dichloromethane / 24 h / -78 - 20 °C

Reference： [1]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[2]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]

42
[ 41777-08-6 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 2: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 3: boron tribromide / dichloromethane
	Multi-step reaction with 4 steps 1: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 2: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 3: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 4: boron tribromide / dichloromethane / 24 h / -78 - 20 °C

Reference： [1]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[2]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]

43
[ 218444-37-2 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With boron tribromide In dichloromethane at -78 - 20℃; for 24h;

Reference： [1]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]

44
C₁₂H₁₀Br₂O₄ [ No CAS ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: boron tribromide / dichloromethane
	Multi-step reaction with 3 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: boron tribromide / dichloromethane / 24 h / -78 - 20 °C

Reference： [1]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[2]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]

45
C₁₀H₈Br₂O₃ [ No CAS ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: boron tribromide / dichloromethane
	Multi-step reaction with 3 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: boron tribromide / dichloromethane / 24 h / -78 - 20 °C

Reference： [1]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]
[2]Rao, Maddali L. N.; Murty, Venneti N.; Nand, Sachchida [Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9415 - 9423]

46
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-diol [ No CAS ]
2-bromobenzofuran-6-ol [ No CAS ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ In water; N,N-dimethyl-formamide for 1h; Inert atmosphere; Heating;

Reference： [1]Sivaraman, Aneesh; Harmalkar, Dipesh S.; Kang, Jiyoon; Choi, Yongseok; Lee, Kyeong [Organic and Biomolecular Chemistry, 2019, vol. 17, # 8, p. 2153 - 2161]

47
[ 106120-04-1 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; potassium phosphate / water; N,N-dimethyl-formamide / 1 h / Inert atmosphere; Heating

Reference： [1]Sivaraman, Aneesh; Harmalkar, Dipesh S.; Kang, Jiyoon; Choi, Yongseok; Lee, Kyeong [Organic and Biomolecular Chemistry, 2019, vol. 17, # 8, p. 2153 - 2161]

48
4-(2,2-dibromovinyl) benzene-1,3-diol [ No CAS ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate; copper(l) iodide / acetonitrile / 3 h / 80 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate / water; N,N-dimethyl-formamide / 1 h / Inert atmosphere; Heating

Reference： [1]Sivaraman, Aneesh; Harmalkar, Dipesh S.; Kang, Jiyoon; Choi, Yongseok; Lee, Kyeong [Organic and Biomolecular Chemistry, 2019, vol. 17, # 8, p. 2153 - 2161]

49
5-((3,5-dimethoxyphenyl)ethynyl)-2-methyl-4H-pyran-4-one [ No CAS ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: indium(III) triflate / tetrahydrofuran / 12 h / 100 °C / Inert atmosphere; Schlenk technique 2: boron tribromide / dichloromethane / 8 h / -78 - 20 °C / Inert atmosphere; Schlenk technique

Reference： [1]Cao, Tongxiang; Jiang, Huanfeng; Zhang, Ling; Zhu, Shifa [Angewandte Chemie - International Edition, 2020, vol. 59, # 12, p. 4670 - 4677][Angew. Chem., 2020, vol. 132, p. 4700 - 4707,8]

50
[ 397333-51-6 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium carbonate; iodine / tetrahydrofuran / 2 h / 20 °C / Schlenk technique; Inert atmosphere 2.1: boron tribromide / dichloromethane / 24 h / -78 - 25 °C / Schlenk technique; Inert atmosphere 2.2: Schlenk technique; Inert atmosphere; Cooling with ice

Reference： [1]Che, Chi-Ming; Wu, Kai; Wu, Liang-Liang; Zhou, Cong-Ying [Angewandte Chemie - International Edition, 2020, vol. 59, # 37, p. 16202 - 16208][Angew. Chem., 2020, vol. 132, # 37, p. 16336 - 16342,7]

51
6-diazo-3-methoxycyclohexa-2,4-dien-1-one [ No CAS ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone; dichloromethane / 7 h / 55 °C / Schlenk technique; Inert atmosphere; Sealed tube 2.1: potassium carbonate; iodine / tetrahydrofuran / 2 h / 20 °C / Schlenk technique; Inert atmosphere 3.1: boron tribromide / dichloromethane / 24 h / -78 - 25 °C / Schlenk technique; Inert atmosphere 3.2: Schlenk technique; Inert atmosphere; Cooling with ice

Reference： [1]Che, Chi-Ming; Wu, Kai; Wu, Liang-Liang; Zhou, Cong-Ying [Angewandte Chemie - International Edition, 2020, vol. 59, # 37, p. 16202 - 16208][Angew. Chem., 2020, vol. 132, # 37, p. 16336 - 16342,7]

52
[ 40925-70-0 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium nitrite; hydrogenchloride / ethanol; water / 2.17 h / 0 °C / Schlenk technique; Inert atmosphere 2.1: potassium carbonate / acetone; dichloromethane / 7 h / 55 °C / Schlenk technique; Inert atmosphere; Sealed tube 3.1: potassium carbonate; iodine / tetrahydrofuran / 2 h / 20 °C / Schlenk technique; Inert atmosphere 4.1: boron tribromide / dichloromethane / 24 h / -78 - 25 °C / Schlenk technique; Inert atmosphere 4.2: Schlenk technique; Inert atmosphere; Cooling with ice

Reference： [1]Che, Chi-Ming; Wu, Kai; Wu, Liang-Liang; Zhou, Cong-Ying [Angewandte Chemie - International Edition, 2020, vol. 59, # 37, p. 16202 - 16208][Angew. Chem., 2020, vol. 132, # 37, p. 16336 - 16342,7]

53
[ 41046-70-2 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 0.08 h / Inert atmosphere 1.2: 15 h / Inert atmosphere 2.1: boron tribromide / dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere

Reference： [1]BasavanaGowda, Melanayakanakatte Kuberappa; Chae, Hee-Sung; Choi, Won Jun; Masagalli, Jagadeesh Nagarajappa [Molecules, 2021, vol. 26, # 5]

54
[ 171290-52-1 ]
[ 56317-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 0.08 h / Inert atmosphere 1.2: 15 h / Inert atmosphere 2.1: boron tribromide / dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere

Reference： [1]BasavanaGowda, Melanayakanakatte Kuberappa; Chae, Hee-Sung; Choi, Won Jun; Masagalli, Jagadeesh Nagarajappa [Molecules, 2021, vol. 26, # 5]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	56317-21-6	MDL No. :	MFCD17166969
Formula :	C₁₄H₁₀O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LHPRYOJTASOZGJ-UHFFFAOYSA-N
M.W :	242.23 g/mol	Pubchem ID :	185848
Synonyms :	1. Moracin M

Num. heavy atoms :	18
Num. arom. heavy atoms :	15
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	3.0
Molar Refractivity :	67.72
TPSA :	73.83 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.7 cm/s

Log Po/w (iLOGP) :	1.69
Log Po/w (XLOGP3) :	2.92
Log Po/w (WLOGP) :	3.22
Log Po/w (MLOGP) :	1.2
Log Po/w (SILICOS-IT) :	2.47
Consensus Log Po/w :	2.3

[ CAS No. 56317-21-6 ]

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Medicinal Chemistry

Safety of [ 56317-21-6 ]

Application In Synthesis of [ 56317-21-6 ]

[ 56317-21-6 ] Synthesis Path-Downstream 1~54

Precautionary Statements-General

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Inquiry

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

Log S (ESOL) :	-3.73
Solubility :	0.0449 mg/ml ; 0.000185 mol/l
Class :	Soluble
Log S (Ali) :	-4.13
Solubility :	0.0179 mg/ml ; 0.0000738 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.08
Solubility :	0.0199 mg/ml ; 0.0000822 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.81

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling