Cyclopentadiene → 1,4-Methanonaphthalene

HRID 1534427Notes

Reaction equation

HRID 1534427 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.[CH:9]1[CH2:13][CH:12]=[CH:11][CH:10]=1.[Mg].O1CCCC1>O>[C:10]12[CH2:9][C:13](=[CH:12][CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]2=1

Participants

6

Reactant 4

HCID 7612CyclopentadieneHCID 8028TetrahydrofuranHCID 114151-Bromo-2-iodobenzeneHCID 5462224Magnesium

Product 1

HCID 566125711,4-Methanonaphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Bromo-2-iodobenzene (1 ml) was combined with cyclopentadiene (1.5 ml) and added dropwise to a mixture of magnesium (0.25 g) and tetrahydrofuran (25 ml) which had been heated to reflux. After the addition, heating was continued for 1 hour. The mixture was cooled to room temperature, treated with water (50 ml), and extracted with ether (3×30 ml). The combined organic layers were dried over magnesium sulfate and the solvents removed on a rotary evaporator. The residue was distilled on a Kugelrohr apparatus (40° C. at 0.1 mm Hg) to provide the product as a yellow oil.

Workup

  1. temperaturehad been heated to reflux
  2. additionAfter the addition
  3. temperatureheating
  4. extractionextracted with ether (3×30 ml)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. customthe solvents removed on a rotary evaporator
  7. distillationThe residue was distilled on a Kugelrohr apparatus (40° C. at 0.1 mm Hg)

Sources & evidence

ORD record
ord-4a8dd784994548d2b5c3fc7dc37268c6
Source dataset
uspto-grants-1992_02
Patent number
US05089506

Reaction notes

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