Iodine → 3-Chloro-2,4,5-trifluorobenzoic Acid

HRID 622580Notes

Reaction equation

HRID 622580 reaction equation
ClCl.[F:3][C:4]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].II.[Cl:17]S(O)(=O)=O>>[Cl:17][C:12]1[C:4]([F:3])=[C:5]([CH:9]=[C:10]([F:14])[C:11]=1[F:13])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 4

HCID 807IodineHCID 24526ChlorineHCID 24638Chlorosulfonic acidHCID 5211702,4,5-Trifluorobenzoic acid

Product 1

HCID 27342693-Chloro-2,4,5-trifluorobenzoic Acid

Procedure

A steady stream of chlorine gas was bubbled through a solution of 8.1 g (46 mmol) of 2,4,5-trifluorobenzoic acid, (*Jpn. Kokai Tokkyo Koho JP 58, 150, 543 Sept. 7, 1983.) 0.2 g (catalytic amount) of iodine, and 15 ml of chlorosulfonic acid at 60° C for four hours. The reaction mixture was cooled to room temperature and poured cautiously onto ice with constant stirring. The suspension was extracted with ethyl acetate, and the extracts were combined, washed with water, and dried over magnesium sulfate. The solvent was evaporated to give 9.4 g of the title compound as an orange solid.

Workup

  1. additionpoured cautiously onto ice with constant stirring
  2. extractionThe suspension was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9b4867e73a27440dba71a48f60bf0cc9
Source dataset
uspto-grants-1988_09
Patent number
US04771054

Reaction notes

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