Iodoethane → HCID 58980768, compound

HRID 2112608Notes

Reaction equation

HRID 2112608 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[CH2:10][C:11]([OH:13])=[O:12].I[CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[CH2:10][C:11]([O:13][CH2:15][CH3:16])=[O:12]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 27779512-(2,4,6-Trifluorophenyl)acetic acid

Product 1

HCID 58980768HCID 58980768, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2,4,6-trifluorophenylacetic acid (570 mg, 3.0 mmol), iodoethane (1.56 g, 10 mmol), and potassium carbonate (1.38 g, 10 mmol) in 5 mL of dimethylsulfoxide is stirred at 50° C. for 3 h, and cooled to room temperature. The mixture is partitioned between diethyl ether and water. The organic layer is washed with water, and saturated sodium chloride, dried over magnesium sulfate, and filtered through hydrous magnesium silicate. The filtrate is concentrated to give ethyl 2,4,6-trifluorophenylacetate as a light yellow oil (581 mg, 2.66 mmol).

Workup

  1. temperaturecooled to room temperature
  2. customThe mixture is partitioned between diethyl ether and water
  3. washThe organic layer is washed with water, and saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through hydrous magnesium silicate
  6. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-be84e9b5b90c4cc4a4d94ae55d4b5a94
Source dataset
uspto-grants-2009_04
Patent number
US07524849B2

Reaction notes

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