Cyclopentadiene → HCID 67452497, compound

HRID 1897746Notes

Reaction equation

HRID 1897746 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Cl)[C:3]=1[Cl:9].C1COCC1.C([Mg]Cl)(C)C.[CH:20]1[CH2:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[Cl:9][C:3]1[CH:2]=[CH:7][CH:6]=[C:5]2[C:4]=1[CH:24]1[CH2:23][CH:22]2[CH:21]=[CH:20]1

Participants

6

Reactant 4

HCID 7612CyclopentadieneHCID 8028TetrahydrofuranHCID 420661-Bromo-2,3-dichlorobenzeneHCID 178418918HCID 178418918, compound

Product 1

HCID 67452497HCID 67452497, compoundYield 117.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-10 °C

Procedure

115 g of 1-Bromo-2,3-dichlorobenzene was dissolved in 470 g of toluene and the solution was cooled down to −10° C. Then a 20% THF solution of isopropylmagnesium chloride (309 g) was added over 30 min and the reaction mixture was stirred 1 hour at −10° C. Freshly distilled cyclopentadiene (44.5 g, 1.3 eq) was added over 10 min. After one hour stirring at ambient temperature, the mixture was heated to reflux. When the conversion was completed, the reaction mixture was filtered off and washed twice with toluene. The mother liquor was evaporated and 106 g of brown crude oil was obtained (yield: 91.5%. The material can be purified by distillation or by CC (silica gel, eluant: Hept/TBME 19/1).

Workup

  1. stirringAfter one hour stirring at ambient temperature
  2. temperaturethe mixture was heated to reflux
  3. filtrationthe reaction mixture was filtered off
  4. washwashed twice with toluene
  5. customThe mother liquor was evaporated

Sources & evidence

ORD record
ord-b9deb7524bff4e848fc09f2229560964
Source dataset
uspto-grants-2013_08
Patent number
US08519152B2

Reaction notes

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