Sodium Carbonate → HCID 58261859, compound

HRID 1618944Notes

Reaction equation

HRID 1618944 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][CH:7]=1.[C:9]1([C:15]2[CH:33]=[C:32](B(O)O)[C:18]3[O:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)=[CH:22][C:21]=4[C:17]=3[CH:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:25]2[C:20]3[O:19][C:18]4[CH:32]=[CH:33][C:15]([C:9]5[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=5)=[CH:16][C:17]=4[C:21]=3[CH:22]=[C:23]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:24]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 58261971HCID 58261971, compound

Product 1

HCID 58261859HCID 58261859, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
110 °C

Procedure

In a 100 mL three-neck flask were put 1.7 g (6.0 mmol) of 3-bromoiodobenzene and 2.2 g (6.0 mmol) of 2,8-diphenyldibenzofuran-4-boronic acid. The air in the flask was replaced with nitrogen. To this mixture were added 30 mL of toluene and 6.0 mL of an aqueous solution of sodium carbonate (2.0 mol/L). While the pressure was reduced, this mixture was stirred to be degassed. To this mixture was added 0.35 g (0.30 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was refluxed at 110° C. for 4 hours. After reaction, the aqueous layer was extracted with ethyl acetate, and the ethyl acetate solution and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate. Then, this mixture was gravity filtered. The resulting filtrate was concentrated to give an oily substance, and the oily substance was dissolved in about 10 mL of toluene. This solution was suction-filtered through Celite (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). The resulting filtrate was concentrated to give an oily substance, and hexane was added to the oily substance. The mixture was irradiated with ultrasonic waves, whereby a solid was precipitated. This solid was collected by suction filtration to give 1.2 g of a white powder in 44% yield, which was the substance to be produced.

Workup

  1. customIn a 100 mL three-neck flask were put
  2. customto be degassed
  3. customAfter reaction
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe resulting filtrate was concentrated
  9. customto give an oily substance
  10. filtrationThis solution was suction-filtered through Celite (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135)
  11. concentrationThe resulting filtrate was concentrated
  12. customto give an oily substance, and hexane
  13. additionwas added to the oily substance
  14. customThe mixture was irradiated with ultrasonic waves, whereby a solid
  15. customwas precipitated
  16. filtrationThis solid was collected by suction filtration

Sources & evidence

ORD record
ord-74f293db50f34b44b18cef30a0ff5fb3
Source dataset
uspto-grants-2014_07
Patent number
US08771840B2

Reaction notes

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