Water → HCID 54490493, compound

HRID 1929756Notes

Reaction equation

HRID 1929756 reaction equation
[C:1]([C:3](=[C:8](C(OC(F)(F)F)=O)[C:9]([F:12])([F:11])[F:10])[C:4]([O:6][CH3:7])=[O:5])#[N:2].C(Cl)(=O)C([Cl:23])=O.O>C(Cl)Cl.N1C=CC=CC=1>[C:1]([C:3](=[C:8]([Cl:23])[C:9]([F:12])([F:11])[F:10])[C:4]([O:6][CH3:7])=[O:5])#[N:2]

Participants

6

Reactant 3

HCID 962WaterHCID 65578Oxalyl chlorideHCID 86628631HCID 86628631, compound

Product 1

HCID 54490493HCID 54490493, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the mixture of the compound 2a and 2b (27.6 g) in methylene chloride (200 mL) was added dropwise oxalyl chloride (31.6 mL) and a few drops of pyridine and the mixture was refluxed under heating for 4 hours. The reaction mixture was poured to water gradually and the mixture was extracted with methylene chloride. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give methyl 2-cyano-3-chloro-4,4,4-trifluoro-2-butenoate as a crude product.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 4 hours
  3. extractionthe mixture was extracted with methylene chloride
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4d50dd8cdb7442a0a67cf6cd98b2ba09
Source dataset
uspto-grants-2012_05
Patent number
US08188097B2

Reaction notes

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