Hydrochloric Acid → 4-(Pentafluorosulfanyl)benzoyl chloride

HRID 511911Notes

Reaction equation

HRID 511911 reaction equation
[Cl:1][C:2](Cl)(Cl)[C:3]1[CH:8]=[CH:7][C:6]([S:9]([F:14])([F:13])([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[OH2:17].Cl>>[F:10][S:9]([F:14])([F:13])([F:12])([F:11])[C:6]1[CH:7]=[CH:8][C:3]([C:2]([Cl:1])=[O:17])=[CH:4][CH:5]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 716122604-Trichloromethyl(pentafluorosulfanylbenzene)

Product 1

HCID 27792154-(Pentafluorosulfanyl)benzoyl chlorideYield 42%

Procedure

Into a 50 mL flask equipped with a stirrer were placed 16.08 g (50 mmol) of 4-trichloromethyl(pentafluorosulfanylbenzene) prepared in Example 1 and 406 mg (5 mol %) of FeCl3. The bath was heated to 70° C. to 75° C., and 900 mg (50 mmol) of water was added dropwise over at least 2 hours. HCl gas was generated during the addition. After the addition was complete, the mixture was heated with stirring for 1 hour. This mixture was distilled under reduced pressure to yield 5.59 g of 4-pentafluorosulfanylbenzoic chloride (product yield: 42%).

Workup

  1. customInto a 50 mL flask equipped with a stirrer
  2. temperatureThe bath was heated to 70° C. to 75° C.
  3. additionAfter the addition
  4. temperaturethe mixture was heated
  5. distillationThis mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-b438193e9b2546e08712a3b4e4677931
Source dataset
uspto-grants-2015_08
Patent number
US09102608B2

Reaction notes

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