Potassium Chloride → 3-Chloro-2,4,5-trifluorobenzoyl chloride

HRID 2395891Notes

Reaction equation

HRID 2395891 reaction equation
[Cl-:1].[K+].[Cl:3][C:4]1[C:5]([F:14])=[C:6]([CH:9]=[C:10]([F:13])[C:11]=1[F:12])[CH:7]=[O:8].ClCl>ClC1C=CC=CC=1C(F)(F)F>[Cl:3][C:4]1[C:5]([F:14])=[C:6]([CH:9]=[C:10]([F:13])[C:11]=1[F:12])[C:7]([Cl:1])=[O:8]

Participants

5

Reactant 3

HCID 4873Potassium ChlorideHCID 24526ChlorineHCID 117455413-Chloro-2,4,5-trifluorobenzaldehyde

Product 1

HCID 27822453-Chloro-2,4,5-trifluorobenzoyl chlorideYield 376.2%

Reagents, catalysts & solvents 1

HCID 69211-Chloro-2-(trifluoromethyl)benzeneSolvent2×

Procedure

100 ml of 2-chlorobenzotrifluoride and 4.5 g of potassium chloride were placed at 110° C. in a chlorination apparatus with UV irradiation and 50 g of 3-chloro-2,4,5-trifluorobenzaldehyde in 50 ml of 2-chlorobenzotrifluoride were subsequently added dropwise with exclusion of air. After addition of 10 ml of the solution, chlorine was added at the rate at which it was absorbed. The metered addition was continued until the entire amount of the aldehyde used had reacted (gas chromatographic monitoring). Distillation of the reaction mixture gave 52 g of 3-chloro-2,4,5-trifluorobenzoyl chloride having a boiling point of 92° C./20 mbar.

Workup

  1. additionwere subsequently added dropwise with exclusion of air
  2. additionwas added at the rate at which it
  3. customwas absorbed
  4. additionThe metered addition
  5. customused had reacted (gas chromatographic monitoring)
  6. distillationDistillation of the reaction mixture

Sources & evidence

ORD record
ord-48d57844bb1b4942bd65261fae2a8ba3
Source dataset
uspto-grants-1996_02
Patent number
US05489715

Reaction notes

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