Iodoethane → HCID 58980768, compound

HRID 1181253Notes

Reaction equation

HRID 1181253 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 magnesol. 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 magnesol
  6. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-f52c97b5d99d4261b80a12d4999ce807
Source dataset
uspto-grants-2007_10
Patent number
US07285555B2

Reaction notes

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