Methanol → Methyl 3-bromo-5-iodobenzoate

HRID 2278746Notes

Reaction equation

HRID 2278746 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].S(Cl)(Cl)=O.[CH3:16]O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([O:7][CH3:16])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 51825203-Bromo-5-iodobenzoic acid

Product 1

HCID 21942573Methyl 3-bromo-5-iodobenzoate

Conditions

Temperature
65 °C

Procedure

A round bottom flask was charged with 3-bromo-5-iodo-benzoic acid (8.00 g, 24.5 mmol) and methanol (50 mL). Thionyl chloride (5.36 mL, 73.4 mmol) was slowly added and the reaction mixture was heated at 65° C. for 1 h. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and washed with aq. NaHCO3. Removal of the solvent under reduced pressure gave the product as a white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with aq. NaHCO3
  4. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-4c7558d90e314d00a465a5c58068a0a6
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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