Ethyl diazoacetate → Ethyl 2-chloro-2-fluorocyclopropanecarboxylate

HRID 1502410Notes

Reaction equation

HRID 1502410 reaction equation
[Cl:1][C:2]([F:4])=[CH2:3].[N+](=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N-]>ClCCl>[Cl:1][C:2]1([F:4])[CH2:3][CH:7]1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 753441-Chloro-1-fluoroethene

Product 1

HCID 9793930Ethyl 2-chloro-2-fluorocyclopropanecarboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of tetrakis(triphenylacetate)dirhodium (3.66 g) and powdered molecule sieves (45 g) in dichloromethane (2.0 L) was added 1-chloro-1-fluoroethene (82 g, 1.02 mol) at −60° C. The reaction mixture was warmed to −35˜−40° C., ethyl 2-diazoacetate (90 g, 790 mmol) in DCM (200 mL) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered and evaporated in vacuo to yield 100 g Ethyl 2-chloro-2-fluorocyclopropanecarboxylate as yellow oil which was used directly in the next step without purification.

Workup

  1. temperatureThe reaction mixture was warmed to −35˜−40° C.
  2. filtrationThe reaction mixture was filtered
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-715ca8f617514ec48ddce59d200b7679
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

Loading…