Sodium chlorodifluoroacetate → HCID 89853502, compound

HRID 931116Notes

Reaction equation

HRID 931116 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.Cl[C:11]([F:16])([F:15])C([O-])=O.[Na+]>C(#N)C>[F:15][CH:11]([F:16])[O:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2734985Sodium chlorodifluoroacetateHCID 178519610HCID 178519610, compound

Product 1

HCID 89853502HCID 89853502, compoundYield 42.85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-hydroxypicolinaldehyde (2 g, 16.24 mmol) in acetonitrile (20 mL) was added sodium 2-chloro-2,2-difluoroacetate (4.46 g, 29.24 mmol) at room temperature. The reaction mixture was heated at 70° C. for 18 h. The reaction mixture was cooled to room temperature and the solid was filtered off. Then the crude material was purified via flash chromatography (100-200 mesh silica gel, 10% ethyl acetate in hexane) to afford the title compound (1.2 g, 42.85%). MS (ES+) (M+H) 174.10

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe solid was filtered off
  3. customThen the crude material was purified via flash chromatography (100-200 mesh silica gel, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bebe60ce42824d1c87a35dcc1467d203
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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