Water → HCID 68960411, compound

HRID 390669Notes

Reaction equation

HRID 390669 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5]Br)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[OH:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[I:24])[C:17]([O:19][CH3:20])=[O:18].O>C(C(C)=O)C.C(OCC)(=O)C>[CH2:1]([O:3][CH2:4][CH2:5][O:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[I:24])[C:17]([O:19][CH3:20])=[O:18])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 611412-Bromoethyl ethyl etherHCID 10378812Methyl 3-hydroxy-4-iodobenzoate

Product 1

HCID 68960411HCID 68960411, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

3.15 g (20 mmol) of 2-bromoethyl ethyl ether and 3.4 g (24.6 mmol) of potassium carbonate are added to a solution of 5.7 g (20 mmol) of methyl 3-hydroxy-4-iodobenzoate (prepared according to Example 19d) in 50 mL of methyl ethyl ketone. The reaction mixture is heated at 80° C. for 12 hours. The reaction is stopped by addition of 50 mL of water and extraction with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then purified by chromatography on a column of silica eluted with an 80/20 heptane/ethyl acetate mixture. 5.93 g (83%) of methyl 3-(2-ethoxyethoxy)-4-iodobenzoate are obtained in the form of a colorless oil.

Workup

  1. dry with materialdried over sodium sulfate
  2. customThe solvents are evaporated off
  3. customthe residue is then purified by chromatography on a column of silica
  4. washeluted with an 80/20 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-30d06bc321f841368bd424e11076f079
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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