Ethylenediamine → Ethyl 2-fluorocyclopropanecarboxylate

HRID 1956830Notes

Reaction equation

HRID 1956830 reaction equation
Br[C:2]1([F:10])[CH2:4][CH:3]1[C:5]([O:7][CH2:8][CH3:9])=[O:6].NCCN>[C].[Pd].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 81%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

An internal glass tube was introduced into an autoclave and 211 mg of ethyl 2-bromo-2-fluoro-1-cyclopropanecarboxylate [obtained in accordance with the method of Bulletin of Faculty of Education, Wakayama University, 33, 33 (1984); cis:trans=0.8:1], 40 mg of 5% palladium-carbon (moisture content: 55% wet) and 8 ml of ethanol were fed thereinto. Then 90 mg of 1,2-diaminoethane was further added and the mixture was stirred at room temperature under an elevated hydrogen gas atmosphere (50 kgf/cm2) for 48 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 95%, the yield was 81% and the cis:trans ratio was 0.8:1.

Workup

  1. customobtained in accordance with the method of Bulletin of Faculty of Education, Wakayama University, 33, 33 (1984)
  2. customAfter the completion of the reaction
  3. filtrationthe catalyst was filtered off
  4. additionThen the reaction mixture containing the title compound

Sources & evidence

ORD record
ord-a23483b85c3847ae89ac28c8fbfe16b5
Source dataset
uspto-grants-1998_07
Patent number
US05780669

Reaction notes

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