Iodoethane → HCID 58980768, compound

HRID 1786303Notes

Reaction equation

HRID 1786303 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-013a65e7184744e295e31a6ef981ae6d
Source dataset
uspto-grants-2009_03
Patent number
US07507739B2

Reaction notes

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