Methanol → Methyl 2-chloro-5-iodobenzoate

HRID 456866Notes

Reaction equation

HRID 456866 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-051f3ce092a4493f9a8a31697cd606f9
Source dataset
uspto-grants-2007_03
Patent number
US07186742B2

Reaction notes

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