Hydrochloric Acid → Methyl 3-bromo-5-iodobenzoate

HRID 431856

Reaction equation

HRID 431856 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([OH:7])=[O:6].Cl.[CH3:13]O>C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([O:7][CH3:13])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 51825203-Bromo-5-iodobenzoic acid

Product 1

HCID 21942573Methyl 3-bromo-5-iodobenzoateYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3-bromo-5-iodobenzoic acid (9.0 g) in methanol (40 mL) was treated with 1M HCl in diethyl ether (27.5 mL). The reaction was heated overnight at 40° C. The solvent was then removed in vacuo, and the residue dissolved in ethyl acetate. The organic solution was washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and concentrated to afford 8.8 g (94%) of methyl 3-bromo-5-iodobenzoate.

Workup

  1. customThe solvent was then removed in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic solution was washed with saturated sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-94a49d8695bb478ca21b31926b752853
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Linked notes

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