Potassium Carbonate → 4-Bromo-3-(3-methoxy-propoxy)-benzoic acid methyl ester

HRID 1158394Notes

Reaction equation

HRID 1158394 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([OH:11])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:20][CH2:21][CH2:22][O:23][CH3:24]>C(#N)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([O:11][CH2:20][CH2:21][CH2:22][O:23][CH3:24])[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6425184Methyl 4-Bromo-3-hydroxybenzoateHCID 135229891-Iodo-3-methoxypropane

Product 1

HCID 592237584-Bromo-3-(3-methoxy-propoxy)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-bromo-3-hydroxy-benzoic acid methyl ester (12 g, 51.9 mmol), potassium carbonate (10.77 g, 77.9 mmol) and 1-iodo-3-methoxy propane (11.42 g, 57.1 mmol) in acetonitrile (250 mL) is stirred at reflux for 16 h. The solvent is concentrated under reduced pressure, H2O (100 mL) is added, and the aqueous layer extracted with ether (50 mL×4). The combined organic extracts are washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title which was used without further purification in the next step. TLC, Rf (hexane/AcOEt 2:1)=0.65. 1H-NMR (CDCl3, 300 MHz): δ=2.12 (p, 2H), 3.38 (s, 3H), 3.63 (t, 2H), 3.9 (s, 3H), 4.2 (t, 2H), 7.5 (d, 1H), 7.55 (m, 1H), 7.6 (d, 1H) ppm.

Workup

  1. temperatureat reflux for 16 h
  2. concentrationThe solvent is concentrated under reduced pressure, H2O (100 mL)
  3. additionis added
  4. extractionthe aqueous layer extracted with ether (50 mL×4)
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto afford the title which
  9. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-08662a074c9d49758389ceba664640fb
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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