Potassium Iodide → Methyl 4-(2-Fluoroethoxy)-2-hydroxybenzoate

HRID 1787930Notes

Reaction equation

HRID 1787930 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Br[CH2:14][CH2:15][F:16].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C.O>[F:16][CH2:15][CH2:14][O:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([OH:1])[CH:11]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 16523Methyl 2,4-Dihydroxybenzoate

Product 1

HCID 10420774Methyl 4-(2-Fluoroethoxy)-2-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

A mixture of methyl 2,4-dihydroxybenzoate (5.04 g, 30 mmol), 1-bromo-2-fluoroethane (4.18 g, 2.46 mL, 33 mmol), potassium carbonate (4.55 g, 33 mmol) and potassium iodide (1 g) in DMF (20 mL) was heated overnight at 55-60° C. before it was poured into water (150 mL). The resulting white precipitate was filtered, redissolved in dichloromethane, dried (MgSO4), concentrated and diluted with hexane to afford the ether in two crops (1.30 g and 2.19 g). The first crop was characterized:

Workup

  1. filtrationThe resulting white precipitate was filtered
  2. dissolutionredissolved in dichloromethane
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. additiondiluted with hexane
  6. customto afford the ether in two crops (1.30 g and 2.19 g)

Sources & evidence

ORD record
ord-2eff0da841654459882383e7c9b1b5c1
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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