Ethylenediamine → Ethyl 2-fluorocyclopropanecarboxylate

HRID 1956831Notes

Reaction equation

HRID 1956831 reaction equation
Br[C:2]1([F:10])[CH2:4][CH:3]1[C:5]([O:7][CH2:8][CH3:9])=[O:6].NCCN>[Ni].C(O)C>[F:10][CH:2]1[CH2:4][CH:3]1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 22371314Ethyl 2-bromo-2-fluoro-1-cyclopropanecarboxylate

Product 1

HCID 10313150Ethyl 2-fluorocyclopropanecarboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

An internal glass tube was introduced into an autoclave and 0.5 g of ethyl 2-bromo-2-fluoro-1-cyclopropanecarboxylate (cis:trans=0.8:1), 0.5 ml of Raney nickel and 5 ml of ethanol were fed thereinto. Then 0.43 g of 1,2-diaminoethane was further added and the mixture was stirred at room temperature under a hydrogen gas atmosphere (1 kgf/cm2) for 24 hours. After the completion of the reaction, the catalyst was filtered off. Then the reaction mixture containing the title compound was analyzed by gas chromatography. As a result, it was found out that the reaction conversion rate was 100%, the yield was 78% and the cis:trans ratio was 0.8:1.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe catalyst was filtered off
  3. additionThen the reaction mixture containing the title compound

Sources & evidence

ORD record
ord-7d778b16408c4cb3bd153380858b0c80
Source dataset
uspto-grants-1998_07
Patent number
US05780669

Reaction notes

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