Benzene → HCID 86755282, compound

HRID 1003634Notes

Reaction equation

HRID 1003634 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[CH:9]1C=C[CH:12]=[CH:11][CH:10]=1.[C:15]([O-:18])([O-])=O.[Na+].[Na+].C[OH:22]>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:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]2[CH:11]=[CH:12][O:22][C:9]=2[CH:15]=[O:18])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 887MethanolHCID 78041,4-DibromobenzeneHCID 10340Sodium Carbonate

Product 1

HCID 86755282HCID 86755282, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

In a 2-neck flask was placed 1,4-dibromobenzene (13.5 g, 57 mmol) with catalyst Pd(PPh3)4 and added 30 mL of benzene and 6 mL of 2 M Na2CO3 aqueous solution. The mixture was then added a methanol solution of dihydroxy-(2-(5-formyl-furyl))borane (2 g, 14 mmol) and heated at reflux for 12 hrs. TLC showed 2 fluorescent spots. The less polar spot was identified as desired dimer product. The mixture was extracted with ether. The combined ether extracts were dried with anhydrous MGSO4 and concentrated. Chromatograph yielded 30% of 1-bromo-4-(2-formylfuryl)benzene. 1H NMR (CDCl3, 200 MHz): δ6.82 (d, J=3.8 Hz, 1H), 7.29 (d, J=3.8 Hz, 1H), 7.45~7.72 (AA'BB', 4H), 9.64 (s, 1H).

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

Sources & evidence

ORD record
ord-e907e7468e0b45f2a793f680fc2c6741
Source dataset
uspto-grants-2000_04
Patent number
US06046229

Reaction notes

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