Benzene → HCID 15434853, compound

HRID 1604454Notes

Reaction equation

HRID 1604454 reaction equation
[Br:1][C:2]1[O:3][C:4](Br)=[CH:5][CH:6]=1.[CH:8]1C=C[CH:11]=[CH:10][CH:9]=1.C([O-])([O-])=[O:15].[Na+].[Na+]>CO.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[O:3][C:4]([C:8]2[O:15][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 108788462,5-dibromofuran

Product 1

HCID 15434853HCID 15434853, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Procedure

In a 2-neck flask was placed 2,5-dibromofuran (18.1 g, 80 mmol) with catalyst Pd(PPh3)4 (5 mol %) and added 30 mL of benzene and 6 mL of 2 M Na2CO3 aqueous solution. The mixture was added 2.2 g (20 mmol) of dihydroxy-2-(furyl) borane dissolved in 6 mL of methanol and heated at reflux for 12 hrs. Thin layer chromatography ("TLC") showed 2 fluorescent spots. The less polar spot was identified as the desired dimer product. The mixture was extracted with ether. The combined ether extracts were dried with anhydrous MgSO4 and concentrated. The crude product was then used for the next reaction.

Workup

  1. customIn a 2-neck flask was placed
  2. temperatureheated
  3. temperatureat reflux for 12 hrs
  4. extractionThe mixture was extracted with ether
  5. dry with materialThe combined ether extracts were dried with anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe crude product was then used for the next reaction

Sources & evidence

ORD record
ord-1f29d136d5734e09a5e4a56c194d17f2
Source dataset
uspto-grants-1999_11
Patent number
US05994394

Reaction notes

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