Silicon tetrachloride → 3,5-Bis(trifluoromethyl)benzoyl chloride

HRID 2229881Notes

Reaction equation

HRID 2229881 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6](F)=[O:7].[Cl-].[Al+3].[Cl-].[Cl-].[Si](Cl)(Cl)(Cl)[Cl:23]>>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6]([Cl:23])=[O:7]

Participants

4

Reactant 3

HCID 24816Silicon tetrachlorideHCID 6451240Aluminum(III) ChlorideHCID 9856492HCID 9856492, compound

Product 1

HCID 1018563,5-Bis(trifluoromethyl)benzoyl chloride

Conditions

Temperature
40 °C

Procedure

1040 g of 3,5-bis(trifluoromethyl)benzoyl fluoride and 24 g of aluminum chloride were initially introduced and heated to 40° C. With stirring, 224 g of silicon tetrachloride were added dropwise over 3 hours, where the temperature was controlled and did not exceed 45° C. The mixture was then stirred until the evolution of gas had stopped (2 hours). 30 g of zeolite X133 were then added, and the mixture was filtered. This gave 1000 g of a cloudy filtrate, which was admixed with 5 g of triphenylphosphine and distilled at 12 mbar over a 70 cm column. This gave 623 g (83.6% of theory) of 3,5-bis(trifluoromethyl)benzoyl chloride which passed over at 68° C. (bath temperature: 80° C.).

Workup

  1. customdid not exceed 45° C
  2. stirringThe mixture was then stirred until the evolution of gas
  3. custom(2 hours)
  4. filtrationthe mixture was filtered
  5. distillationdistilled at 12 mbar over a 70 cm column
  6. custompassed over at 68° C. (bath temperature: 80° C.)

Sources & evidence

ORD record
ord-ecf16ddd89e74edf91f583c32b9d6690
Source dataset
uspto-grants-2002_07
Patent number
US06420601B2

Reaction notes

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