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[ CAS No. 916435-45-5 ] {[proInfo.proName]}

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Product Details of [ 916435-45-5 ]

CAS No. :916435-45-5 MDL No. :MFCD32215230
Formula : C12H6BrIO Boiling Point : -
Linear Structure Formula :- InChI Key :VBKDJWISHQGFML-UHFFFAOYSA-N
M.W : 372.98 Pubchem ID :56649787
Synonyms :

Safety of [ 916435-45-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 916435-45-5 ]

* 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 [ 916435-45-5 ]

[ 916435-45-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 916435-45-5 ]
  • [ 28890-99-5 ]
  • [ 1401068-26-5 ]
YieldReaction ConditionsOperation in experiment
78% With caesium carbonate;copper(l) iodide; L-proline; In dimethyl sulfoxide; at 100℃; for 18h;Inert atmosphere; c) 1.00 g (2.68 mmol) 6-bromo-2-iodo-dibenzofuran, 1.75 g (5.36 mmol) caesium carbonate, 130 mg (0.67 mmol) copper(I) iodide and 150 mg (1.34 mmol) L-proline are added to 670 mg (3.22 mmol) <strong>[28890-99-5]5H-benzimidazo[1,2-a]benzimidazole</strong> in 20 ml DMSO under nitrogen. The reaction mixture is stirred for 18 h at 100 C. and filtered. THF and toluene are added to the organic phase and the organic phase is washed with water. The organic phase is dried with magnesium sulfate and the solvent is distilled off. The product can be used without further purification in step d) (yield=650 mg (78%)).1H NMR (400 MHz, CDCl3): delta 8.66 (d, J=2.2 Hz, 1H), 8.13-8.19 (m, 2H), 7.96-8.07 (m, 3H), 7.66-7.78 (m, 3H), 7.25-7.45 (m, 5H).
78% With copper(l) iodide; caesium carbonate; L-proline; In dimethyl sulfoxide; at 100℃; for 18h;Inert atmosphere; c) 1.00 g (2.68 mmol) 6-bromo-2-iodo-dibenzofuran, 1.75 g (5.36 mmol) caesium carbonate, 130 mg (0.67 mmol) copper(l) iodide and 150 mg (1.34 mmol) L-proline are added to 670 mg (3.22 mmol) 5H-benzimidazo[1 ,2-a]benzimidazole in 20 ml DMSO under nitrogen. The reaction mixture is stirred for 18 h at 100 C and filtered. THF and toluene are added to the organic phase and the organic phase is washed with water. The organic phase is dried with magnesium sulfate and the solvent is distilled off. The product can be used without further purification in step d) (yield = 650 mg (78 %)).1H NMR (400 MHz, CDCI3): delta 8.66 (d, J = 2.2 Hz, 1 H), 8.13-8.19 (m, 2H), 7.96-8.07 (m, 3H), 7.66-7.78 (m, 3H), 7.25-7.45 (m, 5H).
  • 2
  • [ 89827-45-2 ]
  • [ 916435-45-5 ]
YieldReaction ConditionsOperation in experiment
83% With [bis(acetoxy)iodo]benzene; sulfuric acid; iodine; acetic anhydride; acetic acid at 20℃; for 36h; Inert atmosphere;
65% With [bis(acetoxy)iodo]benzene; sulfuric acid; iodine; acetic anhydride; acetic acid at 20℃; for 10h; Inert atmosphere; 1.1 1) Synthesis of Intermediate 1-1 10 g (40.65 mmol) of 4-bromo dibenzofuran under nitrogen,iodine 5.1 g (20.32 mmol),6.6 g (20.32 mmol) of phenyl iodide diacetate150 mL acetic acidInto a 150 mL acetic anhydride mixed solvent, add 3 drops of sulfuric acid,Stir at room temperature for 10 hours.Terminate the reaction,Ethyl acetate is added to the mixed solution, washed with water, the layers are separated, and only the organic layer is added. Anhydrous magnesium sulfate is added and stirred. After filtration through silica pad, the solution was concentrated by column concentration under reduced pressure, and intermediate 1-1 was obtained in 65% yield.
65% With [bis(acetoxy)iodo]benzene; sulfuric acid; iodine; acetic anhydride; acetic acid at 20℃; for 10h; Inert atmosphere; 2.(1) (1) Synthesis of Intermediate 2-1 10.0 g (40.65 mmol) of 4-bromo dibenzofuran, 5.1 g (20.32 mmol) of iodine and 6.6 g (20.32.mmol) of phenyl iodide diacetate were placed in a mixed solvent of 150 mL of acetic acid and 150 mL of acetic anhydride under nitrogen atmosphere. Three drops of sulfuric acid was added drop wisely in the solution and then stirred 10 hours at room temperature. After the reaction was completed, ethyl acetate was added into the mixed solution, and then the solution was washed with water to separate an organic layer from an aqueous layer. Anhydrous magnesium sulfate was added to the organic solution and the organic solution was stirred again. After the solution was filtered with silica pad, the solution was concentrated under reduced pressure and purified by column chromatography to give an Intermediate 2-1 (yield: 65%).
65% With [bis(acetoxy)iodo]benzene; sulfuric acid; iodine; acetic anhydride; acetic acid at 20℃; for 10h; Inert atmosphere; 1.1 (1) Synthesis of Intermediate 1-1 10.0 g (40.65 mmol) of 4-bromo dibenzofuran, 5.1 g (20.32 mmol) of iodine and 6.6 g (20.32 mmol) of phenyl iodide diacetate were placed in a mixed solvent of 150 mL of acetic acid and 150 mL of acetic anhydride under nitrogen atmosphere. Three drops of sulfuric acid were added in the solution and then stirred 10 hours at room temperature. After the reaction was completed, ethyl acetate was added into the mixed solution, and then the solution was washed with water and organic layer was separated from aqueous layer. Anhydrous magnesium sulfate was added to the organic solution and the solution was stirred again. After the solution was filtered with silica pad, the solution was concentrated under reduced pressure and purified by column chromatography to give an Intermediate 1-1 (yield: 65%).
65% With [bis(acetoxy)iodo]benzene; sulfuric acid; iodine; acetic anhydride In acetic acid at 20℃; for 10h; Inert atmosphere; 1.1 (1) Synthesis of Intermediate 1-1 10 g (40.65 mmol) of 4-bromo dibenzofuran, 5.1 g (20.32 mmol) of iodine and 6.6 g (20.32 mmol) of phenyl diacetate were placed into a mixed solvent of 150 mL of acetic acid and 150 mL of acetic anhydride under nitrogen atmosphere, three drops of sulfuric acid was added into the solution with drop-wise, and then the solution was stirred for 10 hours at room temperature. After reaction was completed, ethyl acetate was added into the mixed solution, then the solution was washed with water to separate an aqueous layer form an organic layer. The organic layer was placed into anhydrous magnesium sulfate and then the organic solution was stirred again. The organic solution was filtered with a silica pad, concentrated under reduced pressure and then purified by column chromatography to give intermediate 1-1 (yield: 65%).
60% With [bis(acetoxy)iodo]benzene; sulfuric acid; iodine; acetic anhydride; acetic acid at 20℃; for 36h; Inert atmosphere; 1.1 Step 1: Synthesis of Intermediate Product (Compound 3-A) 4-bromodibenzofuran (2 g, 8.1 mmol), iodobenzene-diacetate (1.3 g, 4.0 mmol) and iodine (1.03 g, 4.0 mmol) were suspended in 10 mL of acetic anhydride and 10 mL of acetic acid. After adding a small amount of sulfuric acid, the mixture was stirred at room temperature under nitrogen flow for 36 hours. Upon completion of the reaction, the organic layer was extracted with dichloromethane. The solution was dried using anhydrous sodium sulfate. After vacuum distillation, the solution was columned and recrystallized with hexane to obtain compound 3-A (1.8 g, yield: 60%).
51% With [bis(acetoxy)iodo]benzene; sulfuric acid; iodine; acetic anhydride; acetic acid at 20℃; for 24h; 8 Synthesis of 6-bromo-2-iododibenzo[b,d]furan A mixture of 24.7 g (100 mmol) 4-bromodibenzo[b,d]furan, 12.7 g (50 mmol) of iodine, 16.1 g (50 mmol) of phenyliododiacetate, 50 ml of acetic acid, 50 ml of acetic anhydride and 3 ml of sulfuric acid were stirred at room temperature for 24 hours. After completion of reaction, toluene was added to the reaction mixture and the mixture was washed with water. After the organic phase was dried with anhydrous magnesium sulfate, the solvent in the organic phase was distilled away under reduced pressure. The residue was purified by column chromatography on silica(hexane-dichloromethane) afforded a white solid (19 g, 51 mmol, 51%)
49% With [bis(acetoxy)iodo]benzene; sulfuric acid; iodine In acetic acid at 20℃; Inert atmosphere; 5.a a) 50 g (0.202 mol) 4-Bromo-dibenzofuran are added to 500 ml acetic acid under nitrogen. At room temperature 32,5 g (0.101 mol) (Diacetoxy-iodo)benzene, 25.7 g (0.101 mol I2 and 16 drops of H2SO4 97% are added in four portions each within 2 h. The resulting suspension is stirred overnight, filtered, the residue is washed three times with cold methanol (50 ml each) and dried at 80°C/125 mbar overnight. The product is crystallized from Cyclohex- ane to yield 36.9 g (49.0% of theory) 6-Bromo-2-iodo-dibenzofuran as a white solid. 1 H-NMR (400 MHz, CDCI3): δ 8.25 (s, 1 H), 7.82 (d, J = 7.6 Hz, 1 H), 7.76 (d, J = 8.4 Hz, 1 H), 7.64 (d, J = 7.6 Hz, 1 H), 7.42 (d, J = 8.4 Hz, 1 H), 7.26 - 7.21 (m, 1 H).
47.7% With [bis(acetoxy)iodo]benzene; sulfuric acid; iodine; acetic anhydride; acetic acid at 20℃; for 10h; Inert atmosphere; 2.3. Synthesis of 2-iodo-6-bromodibenzofuran (2) In a 250 mL round-bottom three-neck flask under a nitrogen atmosphere,4-bromodibenzofuran (5 g, 20 mmol), iodine (2.57 g, 10 mmol),phenyliodine diacetate (3.259 g, 10 mmol), sulfuric acid (0.01 mL),acetic acid (15 mL) and acetic anhydride (15 mL) were placed, andstirred at room temperature for 10 h. The reaction mixture was washedwith water, extracted with dichloromethane, and concentrated to givecompound (2) (3.6 g, 47.7%). 1H NMR (300 MHz, CDCl3) δ 8.27 (s, 1H),7.85 (d, 1H, J =6.0 Hz), 7.78 (d, 1H, J =6.0 Hz), 7.66 (d, 1H, J =9.0Hz), 7.44 (d, 1H, J =6.0 Hz), 7.25 (t, 1H, J =7.5 Hz). 13C NMR (75 MHz,CDCl3) δ 155.41, 153.41, 136.38, 130.79, 130.01, 126.80, 124.37,124.33, 119.80, 114.14, 104.59, 86.35. HRMS (ESI, m/z): [M + H]+calcd for C12H6BrIO, 371.86; found 372.00. Elemental analysis; found:C, 38.38; H, 1.48%; molecular formula C12H6BrIO requires C, 38.64; H,1.62; Br, 21.42; I, 34.02; O, 2.44%.
With [bis(acetoxy)iodo]benzene; sulfuric acid; iodine In acetic anhydride; acetic acid at 20℃;
With [bis(acetoxy)iodo]benzene; sulfuric acid; iodine In acetic anhydride; acetic acid

  • 3
  • [ 916435-45-5 ]
  • [ 1527479-23-7 ]
  • [ 2648141-82-4 ]
YieldReaction ConditionsOperation in experiment
62% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate In ethanol; water; toluene at 76℃; for 18h; Inert atmosphere; 14.2 2) Preparation of intermediate a-II-7 Add 6-bromo-2-iodo dibenzofuran (15.0g, 40.2mmol),Intermediate 1-1 (10.3g, 40.2mmol), tetrakistriphenylphosphine palladium(2.3g, 2.0mmol), potassium carbonate (12.2g, 88.4mmol) and tetrabutylammonium bromide (0.13g, 0.4mmol) were added to a three-necked flask, toluene (120mL),Add ethanol (60mL) and deionized water (30mL) into a three-necked flask,Under the protection of nitrogen, the temperature was increased to 76°C, and the mixture was heated under reflux and stirred for 18 hours.Cool to room temperature, stop stirring, separate the organic phase after the reaction solution is washed with water,Use anhydrous magnesium sulfate to dry, and remove the solvent under reduced pressure to obtain a crude product;Use dichloromethane/n-heptane as the mobile phase to purify the crude product by silica gel column chromatography to obtain the white product intermediate a-II-7(11.6g, yield 62%).
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