Chloride → HCID 10487663, compound

HRID 277179Notes

Reaction equation

HRID 277179 reaction equation
[Cl-].CS(C)=[O:4].ClCCl.[F:9][C:10]1[C:15]2[CH:16]=C(O)[O:18][C:14]=2[C:13]([F:20])=[CH:12][CH:11]=1.C(N([CH2:26][CH3:27])CC)C>O>[F:9][C:10]1[C:15]2[CH:16]=[C:27]([CH:26]=[O:4])[O:18][C:14]=2[C:13]([F:20])=[CH:12][CH:11]=1

Participants

7

Reactant 5

HCID 312ChlorideHCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 8471TriethylamineHCID 22627651HCID 22627651, compound

Product 1

HCID 10487663HCID 10487663, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Oxazalyl chloride (0.26 ml) was added to 0.42 ml dimethyl sulfoxide and 7 ml dichloromethane at −78° C. and stirred for 3 minutes at the same temperature. 272 mg of the 4,7-difluoro-2-hydroxybenzofuran was added thereto at the same temperature and stirred for 40 minutes. After 1.2 ml triethylamine was added to the reaction mixture, the temperature was raised to room temperature, and the mixture was stirred at room temperature for 30 minutes. After water was added to the reaction mixture, it was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then evaporated. The resulting residue was subjected to silica gel chromatography (developing solvent: 5% ethyl acetate/n-hexane) to give 169 mg of 4,7-difluorobenzofuran-2-carbaldehyde as a colorless solid.

Workup

  1. stirringat the same temperature and stirred for 40 minutes
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-b369eee991de406db3487bf9c17b0c14
Source dataset
uspto-grants-2002_03
Patent number
US06355669B1

Reaction notes

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