Methanol → Methyl 3-bromo-5-iodobenzoate

HRID 1454195Notes

Reaction equation

HRID 1454195 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(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([O:7][CH3:17])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 51825203-Bromo-5-iodobenzoic acid

Product 1

HCID 21942573Methyl 3-bromo-5-iodobenzoateYield 96%

Procedure

A stirred, cloudy solution of 3-bromo-5-iodobenzoic acid (10 g, 30.59 mmol) and concentrated sulfuric acid (0.60 mL) in MeOH (65 mL) was heated under reflux for 15 h. The resulting clear, light yellow solution was then allowed to cool to room temperature and was concentrated under vacuum. The residual yellow solid was dissolved in ethyl acetate (100 mL), washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound (10 g, 96% yield) as a light yellow solid: 1H NMR (CD3OD, 500 MHz) δ ppm 3.93 (3H, s), 8.12 (1H, m), 8.15 (1H, m), 8.29 (1H, m). HPLC retention time: 2.335 min (method A). MS (ESI) (M+H)+ 340.00.

Workup

  1. temperatureunder reflux for 15 h
  2. concentrationwas concentrated under vacuum
  3. dissolutionThe residual yellow solid was dissolved in ethyl acetate (100 mL)
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06d4588c702842e0a5f116e90fb7795d
Source dataset
uspto-grants-2009_01
Patent number
US07476764B2

Reaction notes

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