Dimethylformamide → 2,4-Difluorobenzoyl chloride

HRID 1182946Notes

Reaction equation

HRID 1182946 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:15])=O.CN(C=O)C>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:15])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 741022,4-Difluorobenzoic acid

Product 1

HCID 5880812,4-Difluorobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,4-difluorobenzoic acid (0.100 g, 0.633 mmol) in DCM (3.16 ml) were added oxalyl chloride (0.066 ml, 0.759 mmol) and DMF (0.490 μl, 6.33 μmol) at 0° C. The reaction mixture was stirred for overnight at room temperature. The reaction mixture was concentrated in vacuo, which was used for the next step without further purification. 1H-NMR (CDCl3, Varian 400 MHz) δ 6.92-9.98 (1H, m), 7.01-7.06 (1H, m), 8.16-8.22 (1H, m).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, which
  2. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-486d8ccc53ac49ef9c2e6512ecea0811
Source dataset
uspto-grants-2014_03
Patent number
US08664230B2

Reaction notes

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