Dimethyl Sulfoxide → HCID 20439348, compound

HRID 1979518Notes

Reaction equation

HRID 1979518 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([F:15])([C:11]([F:14])([F:13])[F:12])[C:4]([F:10])([F:9])[C:5](I)([F:7])[F:6].[CH:18]1[C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=[C:20](I)[CH:19]=1.CS(C)=O>[Cu].O>[F:1][C:2]([F:17])([F:16])[C:3]([F:15])([C:11]([F:14])([F:13])[F:12])[C:4]([F:10])([F:9])[C:5]([F:7])([F:6])[C:20]1[CH:19]=[CH:18][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 120854-Iodobenzoic acidHCID 2776191Perfluoro-3-methylbutyl iodide

Product 1

HCID 20439348HCID 20439348, compoundYield 29.7%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3-trifluoromethylperfluorobutyl iodide (19.5 g, 50 mmol), p-iodobenzoic acid (12.4 g, 50 mmol), activated copper (15.9 g, 250 mmol) and dried dimethyl sulfoxide (100 ml) is stirred at 130° C. in an autoclave for 14.5 hours. After cooling, the reaction mixture is poured into water (400 ml), and the precipitated solid material is collected by filtration and dried. Then, the solid material is extracted with ethanol (200 ml), and the ethanol extract is concentrated to yield crude p-(3-trifluoromethylperfluorobutyl)benzoic acid (5.8 g). The crude product is recrystallized from ethanol-water. The melting point of the purified product is 189°-190° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated solid material is collected by filtration
  3. customdried
  4. extractionThen, the solid material is extracted with ethanol (200 ml)
  5. extractionthe ethanol extract
  6. concentrationis concentrated

Sources & evidence

ORD record
ord-8c48d23d16f04250b8af599ec2934353
Source dataset
uspto-grants-1984_11
Patent number
US04481149

Reaction notes

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