Oxalyl chloride → HCID 86666737, compound

HRID 1888991Notes

Reaction equation

HRID 1888991 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:16])=O>ClCCl.CN(C=O)C>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 103307052,3-Dichloro-4-fluorobenzoic acid

Product 1

HCID 86666737HCID 86666737, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

2,3-dichloro-4-fluorobenzoic acid (I32) (5.76 g, 27.6 mmol) was suspended in dichloromethane (DCM) (150 mL) at 0° C. and treated with oxalyl chloride (2.89 mL, 33.1 mmol). The mixture was stirred at 0° C. for 10 minutes before 5 drops of DMF were added. The mixture was stirred to room temperature over 4 h. Solvents were removed in vacuo and the residue was azeotroped with toluene (3×100 mL). The residue was used directly in subsequent steps without further purification, assuming 100% yield.

Workup

  1. additionwere added
  2. customSolvents were removed in vacuo
  3. customthe residue was azeotroped with toluene (3×100 mL)
  4. customThe residue was used directly in subsequent steps without further purification

Sources & evidence

ORD record
ord-e095f388132b4e5b8f9c587a9cdc0c8c
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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