Water → HCID 86607608, compound

HRID 2357551Notes

Reaction equation

HRID 2357551 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[N:7][OH:8])=[C:4]([F:11])[C:3]=1[I:12].[Cl:13]N1C(=O)CCC1=O.O>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[N:7][OH:8])[Cl:13])=[C:4]([F:11])[C:3]=1[I:12]

Participants

5

Reactant 3

HCID 962WaterHCID 31398Chlorosuccinimide2×HCID 86607607HCID 86607607, compound

Product 1

HCID 86607608HCID 86607608, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 4-chloro-2-fluoro-3-iodobenzaldehyde oxime (0.860 g, 2.87 mmol) in DMF (5 mL) at RT was added N-chlorosuccinimide (140 mg). The mixture was heated at 55° C. for 5 min. The mixture was allowed to cool below 50° C. and additional N-chlorosuccinimide (282 mg) was added, and heating continued at 55° C. for 20 min. The resulting reaction mixture was allowed to cool to RT and treated with water (20 mL), and extracted with ethyl acetate (3×30 mL). The combined ethyl acetate layers were washed with brine, dried over magnesium sulfate and concentrated to afford 4-chloro-2-fluoro-3-iodobenzoyl chloride oxime as a light yellow amorphous solid. MS (ESI, pos.ion) m/z: 335 (M+1)

Workup

  1. temperatureto cool below 50° C.
  2. temperatureheating
  3. customThe resulting reaction mixture
  4. temperatureto cool to RT
  5. extractionextracted with ethyl acetate (3×30 mL)
  6. washThe combined ethyl acetate layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7da89cbe65a946d78b25b24101adabb8
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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