Potassium Iodide → Methyl 3-bromo-4-isopropoxybenzoate

HRID 273391Notes

Reaction equation

HRID 273391 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].Br[CH:14]([CH3:16])[CH3:15].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:14]([CH3:16])[CH3:15])[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 4778958Methyl 3-bromo-4-hydroxybenzoate

Product 1

HCID 21956810Methyl 3-bromo-4-isopropoxybenzoateYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 3-bromo-4-hydroxybenzoate (15.0 g, 64.9 mmol), 2-bromopropane (7.68 mL, 77.9 mmol) and potassium iodide (1.0 g, 6.49 mmol) in N,N-dimethylformamide (200 mL) was added potassium carbonate (13.5 g, 97.4 mmol) and the mixture was stirred at 80° C. for 2 hrs. The reaction mixture was concentrated under reduced pressure. Brine was added to the obtained residue and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane-hexane/ethyl acetate=9/1) to give the title compound (14.6 g, yield 83%) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionBrine was added to the obtained residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane-hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-dc1c8edaf7f84497a1a3caaf79d1006f
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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