Dimethylformamide → 2,3,4,5-Tetrafluorobenzoyl chloride

HRID 2255202Notes

Reaction equation

HRID 2255202 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4](O)=[O:5].CN(C=O)C.C(Cl)(=O)C([Cl:22])=O>C(Cl)Cl>[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4]([Cl:22])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2975492,3,4,5-Tetrafluorobenzoic acid

Product 1

HCID 27336892,3,4,5-Tetrafluorobenzoyl chlorideYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 25 g (130 mmol) 2,3,4,5-tetrafluorobenzoic acid, 0.5 ml DMF, 200 ml CH2Cl2 and 17 ml (192 mmol) oxalyl chloride was stirred at room temperature for 21 hours. The mixture was filtered and evaporated in vacuo. The concentrate was extracted with 3×300 ml hexane. The extract was filtered via gravity through a coarse pore sintered glass funnel. This filtrate was evaporated in vacuo to yield 22 g (76%) of 2,3,4,5-tetrafluorobenzoylchloride as a colorless liquid. 1H-NMR(CDCl3) δ281-289 (m, 1H); 13C-NMR(CDCl3): δ114.882 (d, J=21.7 Hz), 141.300 (d, J=270.0 Hz), 144.763 (d, J=279 Hz), 146.303 (d, J=241 Hz), 147.595 (d, J=279 Hz), 160.593.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated in vacuo
  3. extractionThe concentrate was extracted with 3×300 ml hexane
  4. filtrationThe extract was filtered via gravity through a coarse pore sintered glass funnel
  5. customThis filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-93d1f81bc0824a1f9ecb5899db4c7738
Source dataset
uspto-grants-1993_08
Patent number
US05238954

Reaction notes

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