Alternatived Products of [ 1008106-86-2 ]
Alternatived Products of [ 1008106-86-2 ]
Product Details of [ 1008106-86-2 ]
| CAS No. : | 1008106-86-2 |
MDL No. : | MFCD09743934 |
| Formula : |
C6H6BIO2
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | N/A |
| M.W : | 247.83 g/mol |
Pubchem ID : | 24866232 |
| Synonyms : |
|
Safety of [ 1008106-86-2 ]
Application In Synthesis of [ 1008106-86-2 ]
- Upstream synthesis route of [ 1008106-86-2 ]
- Downstream synthetic route of [ 1008106-86-2 ]
- 1
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[ 1008106-86-2 ]
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[ 533-58-4 ]
| Yield | Reaction Conditions | Operation in experiment |
| 93% |
With [bis(acetoxy)iodo]benzene; water; triethylamine In acetonitrile at 20℃; for 0.166667h; |
General procedure for syntheses of aromatic alcohols
General procedure: To a stirred solution of appropriate organoboronic acids (0.5 mmol, 1.0 equiv.) and Et3N(1.0 mmol, 2.0 equiv.) in CH3CN(acetonitrile: 3 mL, H2O: 11µL, 0.6mmol, 1.2 equiv.), DAIB (0.75 mmol, 1.5 equiv.), dissolved in acetonitrile (2mL) was added drop wise at room temperature and the mixture was allowed to stir for 10 minutes at that temperature. After completion of the reaction indicated by TLC, the reaction mixture was washed with distilled water (3×7 mL) and extracted with CH2Cl2(3×10 mL). The combined organic phase was dried over Na2SO4 and after evaporating the solvent, the residue was purified by column chromatography over silica gel using hexane/EtOAc as eluent to provide the pure target product. |
| 89% |
With dihydrogen peroxide In neat (no solvent) at 30℃; for 0.0833333h; Green chemistry; |
General procedure for the preparation of compound 3:
General procedure: A mixture of arylboronic acid (1.0 mmol), 30% H2O2 (2 mL), and Amberlite IR-120 resin (15 mg) was stirred at room temperature for the time indicated in Table 2. After completion of the reaction (indicated by TLC) the solid was separated by filtration,extracted with EtOAc (10 mL), washed with 10% NaHCO3 (2 5 mL), and the organic layer was evaporated to give the desired product without further purification. |
| 80% |
With p-benzoquinone; potassium hydroxide In water for 42h; Reflux; Green chemistry; |
Phenols 2a-r; General Procedure
General procedure: A mixture of 1,4-benzoquinone (32.4 mg, 0.3 mmol), boronic acid 1 (1 mmol), and KOH (168 mg, 3.0 mmol) in H2O (5 mL) was stirred at reflux temperature under air for 15-45 h. After the full consumption of 1 (monitored by TLC, eluent: PE-EtOAc, 10:1), the reaction was quenched carefully with aq 2 M HCl (15 mL). The resulting mixture was extracted with EtOAc (3 × 20 mL). The combined organic layers were washed with H2O (30 mL) and brine (10 mL), and dried (Na2SO4). After the removal of the solvent, the resulting residue was purified by chromatography (silica gel, 20 % EtOAc in PE) to give the respective products 2. |
| 66% |
With sodium periodate; iodobenzene In water; acetonitrile at 80℃; for 8h; |
General procedure forsyntheses of aromatic alcohols
General procedure: Toa stirred solution of appropriate organoboronic acids (1.0 mmol, 1.0 equiv.)and NaIO4 (2.0 mmol, 2.0 equiv.) in CH3CN-H2O (acetonitrile: 6 mL, H2O: 2 mL), iodobenzene (0.1 mmol, 10 mol%) was added and the mixture was heated at 80 0C for 8 h. The mixture was cooled and concentrated under vacuum. It was then washed with distilled water (3×4 mL) and extracted with CH2Cl2 (3×7 mL). The combinedorganic phase was dried over Na2SO4 and after evaporating the solvent, the residue was purified by column chromatography over silica gelusing hexanes/EtOAc as eluent to provide the pure target product. |
Reference：
[1]Chatterjee, Nachiketa; Chowdhury, Hrishikesh; Sneh, Kumar; Goswami, Avijit
[Tetrahedron Letters, 2014, vol. 56, # 1, p. 172 - 174]
[2]Mulakayala, Naveen; Ismail; Kumar, Kottur Mohan; Rapolu, Rajesh Kumar; Kandagatla, Bhaskar; Rao, Pallavi; Oruganti, Srinivas; Pal, Manojit
[Tetrahedron Letters, 2012, vol. 53, # 45, p. 6004 - 6007,4]
[3]Cheng, Guolin; Zeng, Xiaobao; Cui, Xiuling
[Synthesis, 2014, vol. 46, # 3, p. 295 - 300]
[4]Chatterjee, Nachiketa; Goswami, Avijit
[Tetrahedron Letters, 2015, vol. 56, # 12, p. 1524 - 1527]
- 2
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[ 1008106-86-2 ]
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[ 1006-47-9 ]
- 3
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[ 1008106-86-2 ]
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[ 42182-27-4 ]
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[ 1445436-66-7 ]
- 4
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[ 20358-00-3 ]
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[ 1008106-86-2 ]
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[ 1403604-85-2 ]
- 5
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[ 2715-68-6 ]
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[ 1008106-86-2 ]
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[ 1393886-02-6 ]
- 6
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[ 1008106-86-2 ]
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[ 100959-22-6 ]
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methyl 2'-iodo-5-nitrobiphenyl-2-carboxylate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 4.9 g |
|
In a reaction flask, 5.0 g of <strong>[100959-22-6]methyl 2-bromo-4-nitrobenzoate</strong>, 4. Og of 2-iodobenzeneboronic acid and 5 g of potassium carbonate were added toVolume ratio of 10: 1 DME and water mixed solution 120mL, nitrogen under the protection of room temperature stirring 30min, then add the catalyst tetrakis (triphenylphosphine) palladium lg, stir under the nitrogen uniform, slowly raise the temperature to l The reaction was complete, the solvent was distilled off under vacuum, the residue was added to methylene chloride and washed twice with pure water 50mL. The organic phase was dried over anhydrous sodium sulfate and evaporated. Except that the solvent was separated and purified by silica gel column chromatography to obtain pure 2'-iodo-5-nitrobiphenyl-2-carboxylate. |
- 7
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[ 1008106-86-2 ]
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[ 2417-10-9 ]
- 8
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[ 1008106-86-2 ]
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[ 108238-09-1 ]
- 9
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[ 1008106-86-2 ]
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[ 2243-47-2 ]
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C18H16BNO2
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 88% |
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 110℃; |
1 Synthesis of intermediate B
In a dry 2L three-necked flask, 37.2 g of 2-iodophenylboronic acid and 28 g of 3-aminobiphenyl were added. Then dry and degassed 600 mL of toluene was added as a solvent. Add 43.2g of sodium tert-butoxide, 0.7g catalyst palladium acetate (2% mol) and 3.7g ligand 1,1'-binaphthyl-2,2'-bisdiphenylphosphine (BINAP, 4% mol). The temperature was raised to 110°C and the reaction was completed overnight. Cool to room temperature Add activated carbon adsorption, suction filtration, remove the solvent, Recrystallization from toluene and ethanol gave 38.2 g of intermediate B (yield 88%). |
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