Thionyl Chloride → HCID 23652403, compound

HRID 534789Notes

Reaction equation

HRID 534789 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.S(Cl)([Cl:24])=O>O1CCOCC1>[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([Cl:24])=[O:16])=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 133462254-[4-(Trifluoromethyl)benzoyl]benzoic acid

Product 1

HCID 23652403HCID 23652403, compoundYield 134.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-{[4-(Trifluoromethyl)phenyl]carbonyl}benzoic acid (200 mg, 0.68 mmol) was stirred in dioxane (5 mL) and thionyl chloride (0.496 mL, 6.8 mmol) added. The reaction mixture was heated at reflux for 1 h. Further thionyl chloride (0.496 mL, 6.8 mmol) was added and heating continued for 3 h. On cooling, the reaction mixture was concentrated in vacuo to give 4-{[4-(trifluoromethyl)phenyl]carbonyl}benzoyl chloride as an oily white liquid (0.286 g) which was used directly in step 2.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. temperatureheating
  4. temperatureOn cooling
  5. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-e5d0f83646d54e88aa885335ecddc882
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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