Ethyl diazoacetate → Ethyl 2-chloro-2-fluorocyclopropanecarboxylate

HRID 468893

Reaction equation

HRID 468893 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

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-90142c9aad19424c8b03237cfe4a2951
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Linked notes

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