Hydrochloric Acid → Methyl 3-bromo-5-iodobenzoate

HRID 378168

Reaction equation

HRID 378168 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([I:12])[CH:11]=1)[C:6]([OH:8])=[O:7].[C:13]([O-])(O)=O.[Na+]>CO>[CH3:13][O:7][C:6](=[O:8])[C:5]1[CH:4]=[C:3]([Br:2])[CH:11]=[C:10]([I:12])[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 51825203-Bromo-5-iodobenzoic acid

Product 1

HCID 21942573Methyl 3-bromo-5-iodobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (40 mL) was added to a 250 mL round bottom flask followed by 60 mL of a solution saturated with anhydrous hydrochloric acid. 3-bromo-5-iodobenzoic acid (Aldrich)(5.02 g, 0.015 mole) was then added and the reaction mixture was stirred at room temperature for 6 hours. The reaction mixture was poured into chilled saturated NaHCO3 solution (700 mL). The mixture was extracted 3× with methylene chloride (100 mL). The organic layers were combined, dried over MgSO4 and concentrated under vacuum to yield methyl-5-bromo-3-iodobenzoate (5.08 g) as a pink solid. MP=55-57° C. MS and NMR were consistent with the desired structure.

Workup

  1. additionThe reaction mixture was poured
  2. extractionThe mixture was extracted 3× with methylene chloride (100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f3727634fd1140869e6dabd58759f31a
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Linked notes

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