Ethyl bromoacetate → 2-((Ethoxycarbonyl)methoxy)-5-iodobenzoic acid methyl ester

HRID 751274Notes

Reaction equation

HRID 751274 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[OH:11].Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].[K]>CC(C)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 248910Methyl 5-IodosalicylateHCID 5462222Potassium

Product 1

HCID 684913212-((Ethoxycarbonyl)methoxy)-5-iodobenzoic acid methyl esterYield 96.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Reflux a mixture of 2-hydroxy-5-iodo-benzoic acid methyl ester (TCI; 5.5 g, 20 mmol) and ethyl bromoacetate (Aldrich; 6.7 g, 40 mmol) in acetone (60 mL) in the presence of potassium (5.5 g, 40 mmol) for 3 h. Filter out the solid and evaporate acetone to give a white residue. Dissolve the residue in ethyl acetate and wash with brine. Evaporate the solvent in vacuum to give final product as a white solid (7 g, 96%). MS (electrospray, m/z) 365 (M+1). 1H NMR (400 MHz, CDCl3) δ 8.1 (d, J=2.0 Hz, 1H), 7.70 (dd, J=8.8, 2.8 Hz, 1H), 6.6 (d, J=8.8 Hz, 1H), 4.68 (s, 2H), 4.3 (q, J=6.8 Hz, 2H), 3.9 (s, 1H), 1.3 (t, J=6.8 Hz, 3H).

Workup

  1. temperatureReflux
  2. filtrationFilter out the solid
  3. customevaporate acetone
  4. customto give a white residue
  5. washwash with brine
  6. customEvaporate the solvent in vacuum

Sources & evidence

ORD record
ord-cdf616f380984445bf291af37ad1d2d1
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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