Iodoethane → Ethyl 3-ethoxy-4-iodobenzoate

HRID 1994171Notes

Reaction equation

HRID 1994171 reaction equation
[CH2:1](I)[CH3:2].[CH2:4]([O:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([I:14])=[C:10]([OH:15])[CH:9]=1)[CH3:5].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:4]([O:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([I:14])=[C:10]([O:15][CH2:1][CH3:2])[CH:9]=1)[CH3:5]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 11087596Ethyl 3-hydroxy-4-iodobenzoate

Product 1

HCID 23090718Ethyl 3-ethoxy-4-iodobenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

Reflux 3-hydroxy-4-iodo-benzoic acid (38 g, 144 mmol) and saturated solution of HCl in ethanol (600 mL) overnight. Evaporate the solvent yielding 42 g, 99% of 3-hydroxy -4-iodo-benzoic acid ethyl ester. 1H NMR (300 MHz, CDCl3): δ 1.39 (t, J=7.1 Hz, 3H), 4.36 (q, J=7.1 Hz, 2H), 7.33 (dd, J=8.3 and 2.0 Hz, 1H), 7.64 (d, J=2.0 Hz, 1H), 7.75 (d, J=8.3 Hz, 1H). Add ethyl iodide (33.8 g, 216 mmol) to a solution of 3-hydroxy -4-iodo-benzoic acid ethyl ester (42 g, 144 mmol) and K2CO3 (39.9 g, 288 mmol) in acetonitrile (400 mL) under magnetic stirring. Heat the reaction mixture at 65° C. for 2 hours, allow the mixture to cool and maintain at RT overnight. Evaporate the solvent and add ethyl acetate to the crude. Filter the solid through Celite® and evaporate the solvent. Yield 42 g, 96%. 1H NMR (300 MHz, CDCl3): δ 1.39 (t, J=7.1 Hz, 3H), 1.50 (t, J=7.0 Hz, 3H), 4.16 (q, J=7.0 Hz, 2H), 4.37 (q, J=7.1 Hz, 2H), 7.36 (dd, J=8.1 and 1.8 Hz, 1H), 7.42 (d, J=1.8 Hz, 1H), 7.84 (d, J=8.1 Hz, 1H).

Workup

  1. temperatureto cool
  2. temperaturemaintain at RT overnight
  3. customEvaporate the solvent
  4. additionadd ethyl acetate to the crude
  5. filtrationFilter the solid through Celite®
  6. customevaporate the solvent

Sources & evidence

ORD record
ord-ed201df7087241908958eeca6aa2fbd8
Source dataset
uspto-grants-2010_01
Patent number
US07652064B2

Reaction notes

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