Methanol → Methyl 2-chloro-5-iodobenzoate

HRID 1988364Notes

Reaction equation

HRID 1988364 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12]O>>[CH3:12][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([I:11])[CH:9]=[CH:10][C:2]=1[Cl:1]

Participants

3

Reactant 2

HCID 887MethanolHCID 5196382-Chloro-5-iodobenzoic acid

Product 1

HCID 35563912Methyl 2-chloro-5-iodobenzoate

Procedure

A solution of 2-chloro-5-iodo-benzoic acid (25.63 g, 90 mmol) in methanol (500 mL) saturated with HCL gas was stirred at room temperature for 48 h. The reaction mixture was concentrated in vacuo, diluted with 1:1 ethyl acetate/Diethyl ether and washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound (25.0 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with 1:1 ethyl acetate/Diethyl ether
  3. washwashed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd89e02a7a9f4485bad082d6d4d123d6
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

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