Methanol → Methyl 2-bromo-5-iodobenzoate

HRID 1948559Notes

Reaction equation

HRID 1948559 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27355722-Bromo-5-iodobenzoic acid

Product 1

HCID 50998202Methyl 2-bromo-5-iodobenzoate

Conditions

Temperature
60 °C

Procedure

To a solution of 2-bromo-5-iodobenzoic acid (2-1), 5.0 g, 15.3 mmol, 1.0 equiv) in methanol (45 mL) was added sulfuric acid (1.06 mL, 19.9 mmol, 1.3 equiv). The reaction mixture was stirred for 60 hours at 60° C., then heated to reflux and stirred 24 hours more. The reaction mixture was cooled, partitioned between EtOAc and saturated sodium bicarbonate solution. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organics were dried over anhydrous sodium sulfate, filtered and concentrated to afford the product (2-2) as a white solid. ESI+ MS [M]+ C8H6BrIO2: 340.7 found, 340.9 required.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. stirringstirred 24 hours more
  4. temperatureThe reaction mixture was cooled
  5. custompartitioned between EtOAc and saturated sodium bicarbonate solution
  6. customThe layers were separated
  7. extractionthe aqueous layer extracted with ethyl acetate
  8. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-6b1602bd1b2548d6b4861622874ffd01
Source dataset
uspto-grants-2013_03
Patent number
US08399494B2

Reaction notes

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