Sodium Iodide → HCID 23024267, compound

HRID 1787938Notes

Reaction equation

HRID 1787938 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][O:16][CH3:17].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.[Cl-].[Na+].O>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:14][CH2:15][O:16][CH3:17])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-DihydroxybenzoateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 23024267HCID 23024267, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
57.5 °C

Procedure

A mixture of methyl 2,4-dihydroxybenzoate (5.04 g, 30 mmol), 1-bromo-2-methoxyethane (3.1 mL, 33 mmol), potassium carbonate (4.55 g, 33 mmol) and sodium iodide (1 g) in DMF (20 mL) was heated overnight at 55-60° C. before it was poured into brine (300 mL). The resulting mixture was extracted with ethyl acetate; and the ethyl acetate solution was washed with brine, dried (MgSO4) and evaporated to a residue (6.17 g), which was subjected to preparative HPLC over silica gel, eluting with a gradient of 0-30% ethyl acetate in hexane over 30 min (at 100 mL/min), to afford the ether (2.72 g).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washand the ethyl acetate solution was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated to a residue (6.17 g), which
  5. washeluting with a gradient of 0-30% ethyl acetate in hexane over 30 min (at 100 mL/min)
  6. customto afford the ether (2.72 g)

Sources & evidence

ORD record
ord-51306b4812214cf79eac7b994c37ae78
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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