Acetic Acid → 4-(Pentafluorosulfanyl)benzoyl chloride

HRID 511910Notes

Reaction equation

HRID 511910 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.C(O)(=[O:19])C.N#N.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[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:19])=[CH:4][CH:5]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 947NitrogenHCID 11776TriphenylphosphineHCID 716122604-Trichloromethyl(pentafluorosulfanylbenzene)

Product 1

HCID 27792154-(Pentafluorosulfanyl)benzoyl chlorideYield 56.1%

Conditions

Temperature
70 °C

Procedure

Into a 25 mL flask equipped with a stirrer were placed 10.0 g (31.2 mmol) of the 4-trichloromethyl(pentafluorosulfanylbenzene) prepared in Example 1 and 0.15 g (3 mol %) of FeCl3. To the mixture, 1.87 g (31.2 mmol) of acetic acid was added dropwise at an oil bath temperature of 70° C. in a N2 atmosphere for 3 hours. After the addition was complete, the mixture was heated with stirring at an oil bath temperature of 70° C. for 17 hours. After the mixture was cooled to room temperature, it was mixed with 0.49 g (6 mol %) of triphenylphosphine and was stirred for 3 hours. This mixture was distilled under reduced pressure to yield 4.67 g of 4-pentafluorosulfanylbenzoic chloride (product yield: 56%).

Workup

  1. customInto a 25 mL flask equipped with a stirrer
  2. additionAfter the addition
  3. temperaturethe mixture was heated
  4. temperatureAfter the mixture was cooled to room temperature
  5. stirringwas stirred for 3 hours
  6. distillationThis mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-8c940fe1dc8241d78e376ad0f4909151
Source dataset
uspto-grants-2015_08
Patent number
US09102608B2

Reaction notes

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