Thionyl Chloride → 2,3,4,5-Tetrafluorobenzoyl chloride

HRID 1461387Notes

Reaction equation

HRID 1461387 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[C:14]([F:15])=[C:13]([F:16])[C:12]([F:17])=[CH:11][C:7]=1[C:8](O)=[O:9]>CN(C)C=O>[F:5][C:6]1[C:14]([F:15])=[C:13]([F:16])[C:12]([F:17])=[CH:11][C:7]=1[C:8]([Cl:3])=[O:9]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2975492,3,4,5-Tetrafluorobenzoic acid

Product 1

HCID 27336892,3,4,5-Tetrafluorobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (2.9 L), 2.5 kg 2,3,4,5-tetrafluorobenzoic acid and 14.5 ml dimethylformamide were charged to a 12 L reaction vessel and warmed at 90°-95° C. for about 90 minutes. The excess thionyl chloride was first removed at atmospheric pressure, then in vacuo. The residue was distilled on a steam bath at water pump pressure collecting the fraction with b.p. 65°-70° C. at about 15 mm resulting in 2635 g (96.2%) of pale yellow distillate.

Workup

  1. temperaturewarmed at 90°-95° C. for about 90 minutes
  2. customThe excess thionyl chloride was first removed at atmospheric pressure
  3. distillationThe residue was distilled on a steam bath at water pump pressure
  4. customcollecting the fraction with b.p. 65°-70° C. at about 15 mm
  5. customresulting in 2635 g (96.2%) of pale yellow distillate

Sources & evidence

ORD record
ord-c39c304c137c40659e2d5d5c9f6385e2
Source dataset
uspto-grants-1991_12
Patent number
US05075319

Reaction notes

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